Ammonium formate → 6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one

HRID 1803019Notes

Reaction equation

HRID 1803019 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH2:14][CH2:15][CH2:16][Cl:17])=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:18]([O-])=O.[NH4+:21]>C(N)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:13][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:11][CH3:12])[N:1]=[CH:18][NH:21][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 230329942-Amino-4-methoxy-5-(3-chloropropoxy)benzoic acid

Product 1

HCID 1355897736-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-oneYield 90.2%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
47.5 °C

Procedure

2-amino-4-methoxy-5-(3-chloropropoxy)benzoic acid (450 gm), formamide (2250 ml) and ammonium formate (200 gm) were heated to 170-180° C. for 3-4 hours. The reaction mass was concentrated under reduced pressure at 140-150° C. The residue was stirred in methanol (1000 ml) at 45-50° C. and cooled to 5-10° C. The solid obtained was filtered to yield the title compound (420 gm, 90% yield).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure at 140-150° C
  2. temperaturecooled to 5-10° C
  3. customThe solid obtained
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-6265f294127543ef9d1b5928c01b3d66
Source dataset
uspto-grants-2013_01
Patent number
US08350029B2

Reaction notes

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