(4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid

Base Information

• Chemical Name: (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid
• CAS No.: 1027537-14-9
• Molecular Formula: C₁₂H₁₄N₂O₄
• Molecular Weight: 250.254
• Mol file: 1027537-14-9.mol

Synonyms:

Chemical Property of (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid

There total 13 articles about (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-nitroveratral (22027-96-9) → (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid (1027537-14-9)

Guidance literature:

Multi-step reaction with 13 steps

1: iron dust, 12 M HCl / methanol / 10 h / Heating

2: Na₂CO₃ / diethyl ether; H₂O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h

3: 93 percent / Jones reagent / acetone / 1.) 0 deg C, 30 min; 2.) room temp., 1 h

4: tetrahydrofuran / 2 h / Ambient temperature

5: 2 M aq. NaN₃ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

6: toluene / 0.5 h / Heating

7: toluene / 2 h / 60 °C

8: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h

9: acetonitrile / 1 h

10: NaBH₃CN / acetonitrile / 12 h / 50 °C

11: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating

12: hydrogen, 60percent HClO₄ / Pd-black / acetic acid / 20 h / Ambient temperature

13: 5 M KOH / methanol / 3 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium azide; perchloric acid; jones reagent; 3 A molecular sieve; hydrogen; iron; sodium cyanoborohydride; sodium carbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetic acid; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)85065-1

Reference yield:

3-amino-4,5-dimethoxy-benzaldehyde → (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid (1027537-14-9)

Guidance literature:

Multi-step reaction with 12 steps

1: Na₂CO₃ / diethyl ether; H₂O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h

2: 93 percent / Jones reagent / acetone / 1.) 0 deg C, 30 min; 2.) room temp., 1 h

3: tetrahydrofuran / 2 h / Ambient temperature

4: 2 M aq. NaN₃ / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: toluene / 0.5 h / Heating

6: toluene / 2 h / 60 °C

7: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h

8: acetonitrile / 1 h

9: NaBH₃CN / acetonitrile / 12 h / 50 °C

10: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating

11: hydrogen, 60percent HClO₄ / Pd-black / acetic acid / 20 h / Ambient temperature

12: 5 M KOH / methanol / 3 h / Ambient temperature

With potassium hydroxide; sodium azide; perchloric acid; jones reagent; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; sodium carbonate; palladium on activated charcoal; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetic acid; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)85065-1

Reference yield:

(3-Amino-4,5-dimethoxy-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (137022-81-2) → (4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid (1027537-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1: acetonitrile / 1 h

2: NaBH₃CN / acetonitrile / 12 h / 50 °C

3: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating

4: hydrogen, 60percent HClO₄ / Pd-black / acetic acid / 20 h / Ambient temperature

5: 5 M KOH / methanol / 3 h / Ambient temperature

With potassium hydroxide; perchloric acid; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; palladium; In methanol; ethanol; acetic acid; acetonitrile;

DOI:10.1016/S0040-4020(01)85065-1

upstream raw materials:

(4-Amino-6,7-dimethoxy-1H-indol-3-yl)-acetic acid ethyl ester

5-nitroveratral

(3-Amino-4,5-dimethoxy-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester

3-benzyloxycarbonylamino-4,5-dimethoxybenzaldehyde

Downstream raw materials:

7-<<2-(3,5-dibromo-4-hydroxyphenyl)ethyl>amino>-1,3,4,8-tetrahydropyrrolo<4,3,2-de>quinolin-8-one

discorhabdin C