Page 5 of 8
The Journal of Organic Chemistry
1
8
8.1 Hz 1H), 2.42 (s, 3H), 2.32 (s, 3H). 13C{ H} NMR (100
MHz, DMSO-d ): δ = 161.6, 154.3, 149.1, 144.7, 127.3,
126.2, 125.5, 118.2, 21.4, 21.4.
,7-Dimethoxy-2-methylquinazolin-4(3H)-one (3k) : This
1
6
,7-Dimethoxyquinazolin-4(3H)-one (3d) : This product
1
2
3
4
5
6
7
8
9
was synthesized following the general procedure 2A by
reacting 2-amino-4,5-dimethoxybenzonitrile (89 mg, 0.5
mmol) and methanol (3.6 mL). The title product was a grey
solid (86 mg, 84% isolated). For the 1g scale reaction isolated
yield was 72% (0.83 g). H NMR (400 MHz, DMSO-d
6
38
6
product was synthesized following the general procedure 2A
by reacting 2-amino-4,5-dimethoxybenzonitrile (89 mg, 0.5
mmol) (59 mg, 0.5 mmol) and ethanol (3.6 mL). The title
product was a white solid (86 mg, 78% isolated yield). H
6
): δ = 12.02 (brs, 1H), 7.38 (s,
H), 7.04 (s, 1H), 3.87 (s, 3H), 3.84 (s, 3H), 2.30 (s, 3H).
1
6
): δ =
1
(
=
5
2.06 (brs, 1H), 7.98 (s, 1H), 7.43 (s, 1H), 7.12 (s, 1H), 3.90
1
3
1
s, 3H), 3.86 (s, 3H). C{ H} NMR (100 MHz, DMSO-d
160.0, 154.4, 148.5, 144.9, 143.8, 115.6, 108.0, 104.9, 55.9,
5.7.
-Chloroquinazolin-4(3H)-one (3e) : This product was
6
): δ
1
NMR (500 MHz, DMSO-d
1
1
8
13
1
7
6
C{ H} NMR (100 MHz, DMSO-d ): δ = 161.1, 154.5, 152.5,
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
synthesized following the general procedure 2A by reacting 2-
amino-4-chlorobenzonitrile (76 mg, 0.5 mmol) and methanol
147.9, 145.1, 113.4, 107.5, 104.8, 55.8, 55.6, 21.2.
18
2
-Ethylquinazolin-4(3H)-one (3l) : This product was
(
3.6 mL). The title product was a white solid (83 mg, 92%
synthesized following the general procedure 2A by reacting 2-
aminobenzonitrile (59 mg, 0.5 mmol) and 1-propanol (3.6
mL). The title product was a white solid (70 mg, 81% isolated
1
isolated yield). H NMR (400 MHz, DMSO-d
6
): δ = 8.11 (s,
1H), 8.08 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 1.9 Hz, 1H), 7.52
1
3
1
(dd, J = 8.6, 2.0 Hz, 1H). C{ H} NMR (100 MHz, DMSO-
): δ = 160.3, 149.9, 147.0, 139.0, 128.0, 127.1, 126.4, 121.5.
1
yield). H NMR (400 MHz, DMSO-d
.06 (d, J = 7.9 Hz, 1H), 7.74 (t, J =7.4 Hz, 1H), 7.57 (d, J =
8.2 Hz, 1H), 7.42 (t, J = 7.4 Hz, 1H), 2.60 (q, J =7.36 Hz, 2H),
6
): δ = 12.14 (brs, 1H),
d
6
8
1
8
6-Chloroquinazolin-4(3H)-one (3f) : This product was
synthesized following the general procedure 2A by reacting 2-
amino-5-chlorobenzonitrile (76 mg, 0.5 mmol) and methanol
1
3
1
1.23 (t, J =7.88 Hz, 3H); C{ H} NMR (100 MHz, DMSO-
): δ = 161.9, 158.4, 149.0, 134.3, 126.8, 126.0, 125.8, 120.9,
27.9, 11.4.
d
6
(
3.6 mL). The title product was a white solid (63 mg, 70%
1
isolated yield). H NMR (400 MHz, DMSO-d
6
): δ = 12.44
14
2-Ethyl-7-methylquinazolin-4(3H)-one (3m) : This product
was synthesized following the general procedure 2A by
reacting 2-amino-4-methylbenzonitrile (66 mg, 0.5 mmol) and
(
8
brs, 1H), 8.12 (s, 1H), 8.04 (d, J = 2.4 Hz, 1H), 7.82 (dd, J =
1
3
1
.8, 2.5 Hz, 1H), 7.68 (d, J = 8.8 Hz, 1H). C{ H} NMR (100
): δ = 159.8, 147.5, 145.9, 134.4, 131.0,
29.5, 124.8, 123.9.
-Fluoroquinazolin-4(3H)-one (3g) : This product was
MHz, DMSO-d
1
6
1
-propanol (3.6 mL). The title product was a white solid (73
mg, 78% isolated yield). For 1g scale reaction isolated yield
1
8
1
6
6
was 69% (0.98 g). H NMR (400 MHz, DMSO-d ): δ = 12.04
synthesized following the general procedure 2A by reacting 2-
amino-5-fluorobenzonitrile (68 mg, 0.5 mmol) and methanol
(brs, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.38 (s, 1H), 7.25 (d, J =
8.0 Hz, 1H), 2.59 (q, J = 7.4 Hz, 2H), 2.41 (s, 3H) 1.22 (t, J =
7.5 Hz, 3H); C{ H} NMR (100 MHz, DMSO-d ): δ = 161.9,
6
158.5, 149.1, 144.8, 127.5, 126.5, 125.7, 118.5, 27.9, 21.4,
11.4.
13
1
(
3.6 mL). The title product was a white solid (56 mg, 69%
1
isolated yield). H NMR (500 MHz, DMSO-d
6
): δ = 12.31
(brs, 1H), 8.06 (s, 1H), 7.73 (dd, J = 8.6, 2.9 Hz, 1H), 7.71-
1
3
1
7.68 (m, 1H), 7.64 (td, J = 8.6, 3 Hz, 1H). C{ H} NMR (125
MHz, DMSO-d ): δ = 161.0, 160.2, 159.1, 145.2 (d, J = 93.7
Hz), 130.0 (d, J = 8.2 Hz), 123.9 (d, J = 8.2 Hz), 122.7 (d, J =
14
2
-Ethyl-6-methylquinazolin-4(3H)-one (3n) : This product
6
was synthesized following the general procedure 2A by
reacting 2-amino-5-methylbenzonitrile (66 mg, 0.5 mmol) and
2
3.9 Hz), 110.5 (d, J = 23.1 Hz).
1-propanol (3.6 mL). The title product was a white solid (70
1
8
1
2
-Methylquinazolin-4(3H)-one (3h) : This product was
mg, 75% isolated yield). H NMR (400 MHz, DMSO-d
6
): δ =
synthesized following the general procedure 2A by reacting 2-
aminobenzonitrile (59 mg, 0.5 mmol) and ethanol (3.6 mL).
The title product was white a solid (64 mg, 80% isolated
12.04 (brs, 1H), 7.85 (s,1H), 7.56 (dd, J = 8.4, 1.6 Hz, 1H),
7.48 (d, J = 8.3 Hz, 1H), 2.59 (q, J = 7.6 Hz, 2H), 2.40 (s, 3H)
1
3
1
1.22 (t, J = 7.6 Hz, 3H); C{ H} NMR (100 MHz, DMSO-
): δ = 161.8, 157.4, 147.0, 135.5, 135.4, 126.7, 125.1, 120.6,
27.8, 20.7, 11.3.
-Chloro-2-ethylquinazolin-4(3H)-one (3o) : This product
yield). For 1g scale reaction isolated yield was 71% (0.96 g).
d
6
1
6
H NMR (400 MHz, DMSO-d ): δ = 12.18 (brs, 1H), 8.05
(
dd, J = 7.8, 1.1 Hz, 1H), 7.74-7.70 (m, 1H), 7.54 (d, J = 8.0
14
7
13
1
Hz, 1H), 7.40 (t, J = 8.0 Hz, 1H), 2.33 (s, 3H). C{ H} NMR
100 MHz, DMSO-d ): δ = 161.8, 154.3, 149.0, 134.2, 126.6,
125.8, 125.7, 120.7, 21.5.
-Chloro-2-methylquinazolin-4(3H)-one (3i) : This product
was synthesized following the general procedure 2A by
reacting 2-amino-4-chlorobenzonitrile (76 mg, 0.5 mmol) and
(
6
1
-propanol (3.6 mL). The title product was a white solid (67
38
1
7
6
mg, 65% isolated yield). H NMR (400 MHz, DMSO-d ): δ =
was synthesized following the general procedure 2A by
reacting 2-amino-4-chlorobenzonitrile (76 mg, 0.5 mmol) and
ethanol (3.6 mL). The title product was a white solid (58 mg,
12.29 (brs, 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.63 (d, J = 1.9 Hz,
1H), 7.47 (dd, J = 8.5, 2.0 Hz, 1H), 2.61 (q, J =7.60 Hz,
1
3
1
2H),1.23 (t, J =7.4 Hz, 3H); C{ H} NMR (100 MHz,
DMSO-d ): δ = 161.2, 160.1, 150.1, 138.9, 127.8, 126.2,
1
6
1
1
0% isolated yield). H NMR (400 MHz, DMSO-d
6
): δ =
6
2.33 (brs, 1H), 8.05 (d, J = 8.6 Hz, 1H), 7.60 (d, J = 1.6 Hz,
125.9, 119.6, 27.9, 11.2.
1
3
1
H), 7.47 (dd, J = 8.6, 1.8 Hz, 1H), 2.34 (s, 3H). C{ H}
): δ = 161.1, 156.1, 150.1, 138.9,
27.8, 126.2, 125.7, 119.5, 21.5.
,7-Dimethylquinazolin-4(3H)-one (3j) : This product was
2-Ethyl-6,7-dimethoxyquinazolin-4(3H)-one (3p)14: This
product was synthesized following the general procedure 2A
by reacting 2-amino-4,5-dimethoxybenzonitrile (89 mg, 0.5
mmol) and 1-propanol (3.6 mL). The title product was a white
NMR (100 MHz, DMSO-d
6
1
3
9
2
1
synthesized following the general procedure 2A by reacting 2-
amino-4-methylbenzonitrile (66 mg, 0.5 mmol) and ethanol
solid (89 mg, 76% isolated yield). H NMR (400 MHz,
6
DMSO-d ): δ = 11.99 (brs, 1H), 7.40 (s, 1H), 7.07 (s, 1H),
(
3.6 mL). The title product was a white solid (68 mg, 78%
3.88 (s, 3H), 3.84 (s, 3H), 2.58 (q, J =7.6 Hz, 2H),1.22 (t, J
=7.5 Hz, 3H); C{ H} NMR (100 MHz, DMSO-d ): δ =
6
1
13
1
isolated yield); H NMR (400 MHz, DMSO-d
6
): δ = 12.08
(brs, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.36 (s, 1H), 7.26 (d, J =
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