Methyl 4-chloroanthranilate → HCID 11015804, compound

HRID 377600Notes

Reaction equation

HRID 377600 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:13][N:14]1[CH2:23][CH:22]([C:24]2[CH:25]=[C:26]([CH2:30][C:31](Cl)=[O:32])[CH:27]=[CH:28][CH:29]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1>ClC(Cl)C>[CH3:13][N:14]1[CH2:23][CH:22]([C:24]2[CH:25]=[C:26]([CH2:30][C:31]([NH:1][C:2]3[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=3[C:4]([O:6][CH3:7])=[O:5])=[O:32])[CH:27]=[CH:28][CH:29]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 80001Methyl 4-chloroanthranilateHCID 19356146HCID 19356146, compound

Product 1

HCID 11015804HCID 11015804, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

2 g (10.7 mmol) of methyl 2-amino-4-chlorobenzoate are dissolved in 30 ml of dichloroethane and, after addition of 4.0 g of 3-[2-methyl-1,2,3,4-tetrahydro-4-(R,S)-isoquinolinyl]phenylacetyl chloride, dissolved in approximately 20 ml of dichloroethane, the mixture is heated under reflux for three hours. The solvent is then distilled off and the residue worked up as is customary. The residue is purified by chromatography on silica gel/dichloromethane (treated with 1-2% of methanol). Methyl 2-{3-[2-methyl-1,2,3,4-tetrahydro-4-(R,S)-isoquinolinyl]phenyl}acetami-do-4-chlorobenzoate is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for three hours
  3. distillationThe solvent is then distilled off
  4. customThe residue is purified by chromatography on silica gel/dichloromethane (treated with 1-2% of methanol)

Sources & evidence

ORD record
ord-d160db97d06c47ab8c0a423516a33963
Source dataset
uspto-grants-2000_02
Patent number
US06028080

Reaction notes

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