Methanol → HCID 81071596, compound

HRID 2272622Notes

Reaction equation

HRID 2272622 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:19])[CH2:12][CH:13]([CH3:18])[CH2:14][N+:15]([O-])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[Cl-].[Ca+2].[Cl-].CO.O>[Cl-].[Na+].O.[Fe]>[NH2:15][CH2:14][CH:13]([CH3:18])[CH2:12][C:11]([NH:10][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[CH:3]=1)=[O:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 5284359Calcium ChlorideHCID 86729779HCID 86729779, compound

Product 1

HCID 81071596HCID 81071596, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of the compound obtained in Step 2 (21.2 g, 75.26 mmol), iron powder (21.01 g, 376.29 mmol) and calcium chloride (25.06 g, 225.78 mmol) in a mixed solvent of methanol (100 mL) and water (20 mL) was stirred at 60° C. for 3 hr. To the reaction solution was added brine at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane) to give 4-amino-N-(3-chloro-4-cyanophenyl)-3-methylbutanamide (6.02 g, 23.92 mmol, 31.8%) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by NH-silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2dbd33fc7a704ff9b6bdd1c8e6a21aba
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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