Sodium Hydroxide → N-cyclopropyl-4-(hydroxymethyl)pyridine-2-carboxamide

HRID 714453Notes

Reaction equation

HRID 714453 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[CH:9][N:8]=2)=[O:6])[CH2:3][CH2:2]1.[Cl-].[Ca+2].[Cl-].[OH-].[Na+].[BH4-].[Na+]>C(O)(C)C.CO.CC(C)=O.O>[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][N:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 66631638Ethyl 2-(cyclopropylcarbamoyl)pyridine-4-carboxylate

Product 1

HCID 59848863N-cyclopropyl-4-(hydroxymethyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5.45 g (23.27 mmol) of ethyl 2-(cyclopropylcarbamoyl)pyridine-4-carboxylate (Example 51A) and 1.55 g (13.96 mmol) of calcium chloride were dissolved in 56.6 ml of isopropanol and 5.7 ml of methanol. At RT, a solution of 4.6 ml of water, 0.1 g (1.16 mmol) of 45% strength sodium hydroxide solution and 1.06 g (27.92 mmol) of sodium borohydride were slowly added dropwise, and the reaction mixture was stirred at RT overnight. 10 ml of acetone were added, and the reaction mixture was stirred at RT for 2 h. The precipitate was filtered off and washed with isopropanol, and the filtrate was evaporated.

Workup

  1. stirringthe reaction mixture was stirred at RT for 2 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with isopropanol
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-010d99110e3e4588a64de80530878495
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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