Water → Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-ylamino]-benzoic acid

HRID 556462

Reaction equation

HRID 556462 reaction equation
Br[C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[NH2:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(O)(=O)C>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([NH:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=[O:26])([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[C:3](=[O:12])[NH:4]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74193-Aminobenzoic AcidHCID 11430Potassium CarbonateHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57507310Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-ylamino]-benzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (740 mg, 2 mmol), 3-amino-benzoic acid (301 mg, 2.2 mmol) and K2CO3 (552 mg, 4 mmol) in DMF (5 mL) was stirred for 0.5 h and then poured into water (100 mL). The resulting solution was acidified by acetic acid and filtered. The filter cake was washed by water and dried to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid as a pale yellow solid. MS m/z 425 (M−H)−.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed by water
  3. customdried

Sources & evidence

ORD record
ord-e98c257208384491aee51833ae63ce35
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Linked notes

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