Water → HCID 19592460, compound

HRID 613490Notes

Reaction equation

HRID 613490 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[O:14][CH3:15])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])(=[O:3])[CH3:2].[BH4-].[Na+].O>O1CCCC1>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[C:17]([NH:16][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[C:13]2[O:14][CH3:15])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19592461HCID 19592461, compound

Product 1

HCID 19592460HCID 19592460, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-8-(2,6-dichlorobenzoylamino)-4-methoxyquinoline (115 mg) in tetrahydrofuran was added sodium borohydride (16.8 mg) at 0° C., and the mixture was stirred for 30 minutes at the same temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 8-(2,6-dichlorobenzoylamino)-3-(1-hydroxyethyl)-4-methoxyquinoline (85.1 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3a88ba82f2c94497a239a8910347c11a
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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