Oxalyl chloride → HCID 59756881, compound

HRID 2196593Notes

Reaction equation

HRID 2196593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:25][CH2:24][C:23]2[C:22]([C:26](O)=[O:27])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]1=[O:29].C(Cl)(=O)C([Cl:33])=O>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:25][CH2:24][C:23]2[C:22]([C:26]([Cl:33])=[O:27])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]1=[O:29]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 597568872-((6,7-Dimethoxyquinolin-4-yl)methyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

Product 1

HCID 59756881HCID 59756881, compoundYield 113.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-((6,7-dimethoxyquinolin-4-yl)methyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (126 mg, 0.321 mmol) was suspended in dichloromethane (4 mL) then added N,N-dimethylformamide (3-4 drops) and oxalyl chloride (0.442 mL, 0.643 mmol). The reaction mixture was stirred at room temperature for 4.5 hours. The mixture was concentrated under vacuum then dried under high vacuum overnight to afford 2-((6,7-dimethoxyquinolin-4-yl)methyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carbonyl chloride (150 mg) as a light yellow solid. MS (ESI, pos. ion) m/z: 407.1 (M+1) for the methyl ester.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthen dried under high vacuum overnight

Sources & evidence

ORD record
ord-de2ccbac8d3745f19f0e22ee6b3d17ff
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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