2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzamide

Base Information

• Chemical Name: 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzamide
• CAS No.: 246512-44-7
• Molecular Formula: C15H23N3O4
• Molecular Weight: 309.365
• DSSTox Substance ID: DTXSID40469859
• Nikkaji Number: J1.645.364A
• Wikidata: Q82297764
• Mol file: 246512-44-7.mol

Synonyms:246512-44-7;2-amino-4-methoxy-5-(3-morpholinopropoxy)benzamide;Gefitinib impurity 2;2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzamide;Gefitinib Impurity 18;Benzamide, 2-amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]-;2-Amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)-benzamide;2-Amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]benzamide;SCHEMBL3284976;DTXSID40469859;HFUBNPPCNQAACT-UHFFFAOYSA-N;WJA51244;MS-24495;HY-100663;CS-0019903;I11734;A1-01396

Chemical Property of 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzamide

Chemical Property:

• Melting Point: 153.5 °C
• Boiling Point: 460.6±45.0 °C(Predicted)
• PKA: 15.86±0.50(Predicted)
• Density: 1.208±0.06 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 309.16885622
• Heavy Atom Count: 22
• Complexity: 350

Purity/Quality:

97% ^*data from raw suppliers

2-Amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]benzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)N)C(=O)N)OCCCN2CCOCC2

Technology Process of 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzamide

There total 7 articles about 2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzamide 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: 38.0%

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile (675126-27-9) → 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide (246512-44-7)

Guidance literature:

With potassium hydroxide; In tert-Amyl alcohol; at 82 ℃;

DOI:10.1016/j.bmcl.2006.04.080

Reference yield:

2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide (861453-16-9) → 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide (246512-44-7)

Guidance literature:

With hydrogen; nickel; In methanol; at 25 - 30 ℃; for 2h; under 1034.32 - 1292.9 Torr; Product distribution / selectivity;

Reference yield:

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile (675126-28-0) → 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide (246512-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / aq. H₂SO₄; HNO₃; AcOH / 50 h / 20 °C

2: 75 percent / sodium dithionite / H₂O / 20 - 50 °C

3: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C

With potassium hydroxide; sodium dithionite; sulfuric acid; nitric acid; acetic acid; In tert-Amyl alcohol; water;

DOI:10.1016/j.bmcl.2006.04.080

upstream raw materials:

2-amino-4-methoxy-5-[(3-morpholin-4-yl)propoxy]benzonitrile

4-(3-chloropropyl)morpholine

4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile

2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile

Downstream raw materials:

7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one