Ethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate → 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoic acid

HRID 1037681Notes

Reaction equation

HRID 1037681 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=3[C:25]([O:27]CC)=[O:26])[CH:8]=2)[N:3]=1>[OH-].[Na+].C1COCC1>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=3[C:25]([OH:27])=[O:26])[CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 58457203Ethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate

Product 1

HCID 584571912-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 15.3 g of ethyl 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)-quinazolin-6-yl]benzoate in 70 ml of sodium hydroxide solution (2 N) and 100 ml of THF is stirred at 80° C. for 6 h. The mixture is extracted three times with 100 ml of diethyl ether each time, and the aqueous phase is adjusted to pH7, whereupon 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoic acid precipitates out. The precipitate is filtered and dried at 50° C. in a drying cabinet.

Workup

  1. extractionThe mixture is extracted three times with 100 ml of diethyl ether each time
  2. customprecipitates out
  3. filtrationThe precipitate is filtered
  4. customdried at 50° C. in a drying cabinet

Sources & evidence

ORD record
ord-d33b9ccefcc14230b790f2d179a8a79b
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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