Sodium hydride → 4-(4-Formylisoquinolin-1-yloxy)benzamide

HRID 2060854Notes

Reaction equation

HRID 2060854 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=[O:25])=[CH:16][N:15]=1>CN(C=O)C>[CH:24]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=2)=[N:15][CH:16]=1)=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 650524-HydroxybenzamideHCID 180077341-Chloroisoquinoline-4-carbaldehyde

Product 1

HCID 594012974-(4-Formylisoquinolin-1-yloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-hydroxybenzamide (0.96 g, 7.0 mmol) in DMF (15 mL) at rt was added sodium hydride (0.28 g, 7.0 mmol). After 1 h, 1-chloro-isoquinoline-4-carbaldehyde (WO01/53274, 1.34 g, 7.0 mmol) was added and the reaction heated at 120° C. for 16 h. The solvent was removed in vacuo and the residue washed with water (100 mL), ether (50 mL) and MeCN (50 mL) to give the title compound: RT=3.13 min; m/z (ES+)=292.9 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue washed with water (100 mL), ether (50 mL) and MeCN (50 mL)

Sources & evidence

ORD record
ord-62eb1e05bd5a4119914a132344f90a2e
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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