Sodium borohydride → 4-(Hydroxymethyl)-N-methylpyridine-2-carboxamide

HRID 658490Notes

Reaction equation

HRID 658490 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[O:14])[NH:12][CH3:13])[CH:6]=1)C.[BH4-].[Na+]>C(O)C>[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([NH:12][CH3:13])=[O:14])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22832121Ethyl 2-(methylcarbamoyl)pyridine-4-carboxylate

Product 1

HCID 234392774-(Hydroxymethyl)-N-methylpyridine-2-carboxamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methylcarbamoyl-isonicotinic acid ethyl ester (7.77 g, 37.3 mmol) in absolute ethanol (125 mL) was added sodium borohydride (2.82 g, 74.6 mmol, 2.0 eq), and the reaction mixture was stirred at RT under argon for 18 h. The solvent was evaporated under reduced pressure, and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×100 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated at reduced pressure to give 5.36 g (86.5%) of 4-(hydroxymethyl)-N-methylpyridine-2-carboxamide as a colorless solid: MS LC-MS [M+H]+=153.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-59a3c760ccb348af8ec409f9a5ae7cc2
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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