Sodium Hydroxide → N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-8-yl)-4-acetylamino-5-chloro-2-methoxybenzamide

HRID 1872734Notes

Reaction equation

HRID 1872734 reaction equation
[C:1]([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9](Cl)=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].C(NC1C(Cl)=CC(C(O)=O)=C(OC)C=1)(=O)C.[NH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1[CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2.[OH-].[Na+]>ClCCl.C(N(CC)CC)C>[CH3:44][N:41]1[CH2:40][CH2:39][C:38]2[C:43](=[C:34]([NH:33][C:9](=[O:10])[C:8]3[CH:12]=[C:13]([Cl:14])[C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=3[O:15][CH3:16])[CH:35]=[CH:36][CH:37]=2)[CH2:42]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 113799924-Acetamido-5-chloro-2-methoxybenzoyl chlorideHCID 135299172-Methyl-1,2,3,4-tetrahydroisoquinolin-8-amine

Product 1

HCID 18687410N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-8-yl)-4-acetylamino-5-chloro-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a cooled solution of 4-acetylamino-5-chloro-2-methoxybenzoyl chloride, (prepared from 4-acetylamino-5-chloro-2-methoxybenzoic acid, 3.19 g) in dichloromethane was added 8-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (2.1 g) and triethylamine (4 ml). After stirring at room temperature for 2.5h, the mixture was basified with 10% sodium hydroxide. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by chromatography on alumina eluting with chloroform, and then crystallised from ethyl acethate to give the title compound.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on alumina eluting with chloroform
  5. customcrystallised from ethyl acethate

Sources & evidence

ORD record
ord-c320c2fb5d7d4300871fd04a52d3b33a
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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