Sodium hydride → 2-Hydroxyquinoline

HRID 970546Notes

Reaction equation

HRID 970546 reaction equation
[O:1]=[C:2]1[C:11](C#N)=[C:10](N2CCN(C(C3SC=CC=3)=O)CC2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[H-].[Na+]>CN(C=O)C>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 210819432-Oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of Compound 116 (364 mg, 1 mmol) in DMF was added to a stirred suspension of NaH (60% in mineral oil, 44 mg, 1.1 mmol) in DMF at room temperature under argon atmosphere. The solution was stirred at room temperature for 1 h and the corresponding alkyl halide was added via syringe. The solution was further stirred at room temperature for 3 to 48 h (TLC control). The reaction was worked up as described in General Procedure C.

Workup

  1. stirringThe solution was further stirred at room temperature for 3 to 48 h (TLC control)

Sources & evidence

ORD record
ord-e8651656437948a798fd3de6d062ed26
Source dataset
uspto-grants-2007_12
Patent number
US07312220B2

Reaction notes

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