Hydrochloric Acid → HCID 67110152, compound

HRID 1481118Notes

Reaction equation

HRID 1481118 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[C:29]([Cu])#[N:30].O.Cl>CN(C=O)C.C(Cl)Cl>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:29]#[N:30])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 86617067HCID 86617067, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67110152HCID 67110152, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-bromo-6-(2,6-dimethyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (2 g, 4.5 mmol) (prepared according to U.S. Pat. No. 7,928,120) and CuCN (0.81 g, 9.0 mmol) in DMF (30 mL) was refluxed for 1.5 h. The resulting mixture was poured into a mixture of water (200 mL) and CH2Cl2 (200 mL). 4 M HCl was added with vigorous stirring until no solid was observed. The aqueous layer was extracted with additional CH2Cl2, and the organic layers were combined, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (10-80% CH2Cl2/hexanes) to give 1.44 g of the title compound as a pale pink solid. MS: (+) m/z 391.34 (M+1).

Workup

  1. customprepared
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (10-80% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-2a84fa2a869c4edcad4fa54ed46c802b
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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