tert-Butyl 5-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate → 1,1-Dimethylethyl 5-[(5-chloro-2,4-dimethoxybenzoyl)amino]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 1872694Notes

Reaction equation

HRID 1872694 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2.[Cl:19][C:20]1[C:21]([O:31][CH3:32])=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>ClCCl.C(N(CC)CC)C>[Cl:19][C:20]1[C:21]([O:31][CH3:32])=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH:28]=1)[C:25]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)=[O:26]

Participants

5

Reactant 2

HCID 17750539tert-Butyl 5-amino-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 186874425-Chloro-2,4-dimethoxybenzoyl chloride

Product 1

HCID 186873951,1-Dimethylethyl 5-[(5-chloro-2,4-dimethoxybenzoyl)amino]-3,4-dihydro-2(1H)-isoquinolinecarboxylateYield 72.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 5-amino-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline (1 g, 4 mmol) in dichloromethane (30 ml) and triethylamine (3 ml) was added 5-chloro-2,4-dimethoxybenzoyl chloride (1.03 g, 4.4 mmol). After stirring at room temperature for 2h the reaction mixture was diluted with dichloromethane (75 ml) and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, concentrated in vacuo and the residue recrystallised from ethyl acethate/petrol to afford the title compound as a colourless crystalline solid (1.3 g).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe residue recrystallised from ethyl acethate/petrol

Sources & evidence

ORD record
ord-7498b744c70e4b31a3c0f61ba5292481
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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