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

HRID 2304233Notes

Reaction equation

HRID 2304233 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), 730-7.55 (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-e0b978948e1947339462f50af7765a48
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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