Tetrahydrofuran → rac-4-(1-Hydroxyethyl)-N-methylpyridine-2-carboxamide

HRID 714449Notes

Reaction equation

HRID 714449 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:11][CH3:12])=[O:10])[CH:4]=1)=[O:2].O1CCC[CH2:14]1.C[Mg]Br.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[OH:2][CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH:11][CH3:12])=[O:10])[CH:4]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 219638894-formyl-N-methylpicolinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 68047396rac-4-(1-Hydroxyethyl)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 0° C. and under argon, 393 mg (2.394 mmol) of 4-formyl-N-methylpyridine-2-carboxamide Example 42A were initially charged in 66 ml abs. tetrahydrofuran. At 0° C., 343 mg (2.873 mmol) of methylmagnesium bromide [1.4 mol in toluene/tetrahydrofuran 3/1] were added dropwise, and the reaction solution was stirred at this temperature for 1 h. 200 μl of semisaturated aqueous sodium bicarbonate solution and 200 ml of ethyl acetate were added to the reaction solution. The precipitate was filtered off and washed with ethyl acetate. The filtrate was evaporated.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-825df3cf2f284e63927ca94387325f65
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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