2,6-Lutidine → N-(cyanomethyl)-2-hydroxy-4-methoxy-N-methylbenzamide

HRID 639931

Reaction equation

HRID 639931 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][NH:14][CH2:15][C:16]#[N:17].N1C(C)=CC=CC=1C>C(Cl)Cl>[C:16]([CH2:15][N:14]([CH3:13])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[OH:1])#[N:17]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 36652Acetonitrile, 2-(methylamino)-HCID 231185592-Hydroxy-4-methoxybenzoyl chloride

Product 1

HCID 55207279N-(cyanomethyl)-2-hydroxy-4-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-4-methoxybenzoyl chloride (22.19 g, 118.9 mmol) in 500 CH2Cl2 were added (methylamino)acetonitrile (10 g, 142.7 mmol) and 2,6-lutidine (19.1 g, 178.4 mmol). The reaction was stirred at rt overnight. The reaction mixture was then partitioned between EtOAc and 1(N) aq HCl. Organic layer washed with 1(N) aq HCl (2×), dried over Na2SO4 and concentrated to light yellow viscous material (24.63 g, 94%). This material was used in the next step without further purification.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and 1(N) aq HCl
  2. washOrganic layer washed with 1(N) aq HCl (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to light yellow viscous material (24.63 g, 94%)
  5. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-337927e2294b41c7ba3c1c1f19860c77
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Linked notes

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