Water → N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide

HRID 1008485Notes

Reaction equation

HRID 1008485 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:8][CH:7]=[CH:6]2)=[O:2].[BH4-].[Na+].O>O1CCCC1.CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([NH:13][C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[N:8][CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22665740N-(6-formyl-1-isoquinolinyl)benzamide

Product 1

HCID 22665633N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamideYield 102.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1.23 g of 1f in 40 mL of tetrahydrofuran and 15 mL of methanol was added 217 mg sodium borohydride in small portions. After stirring the mixture at ambient temperature for 5 min, 50 mL of water was added and tetrahydrofuran and methanol were removed in vacuo. Brine was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was dried (MgSO4) and concentrated under reduced pressure giving 1.27 g of 1g. 1H-NMR 200 MHz (CDCl3) δ: 4.75 (2H, s), 6.95 (1H, br.s), 7.30-7.55 (7H, m), 8.25-8.38 (2H, m), 8.69 (1H, br.s).

Workup

  1. customtetrahydrofuran and methanol were removed in vacuo
  2. additionBrine was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16a6d096fbb545e89383de49d189ad84
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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