Methylamine → 3-(2-bromo-6-chlorophenyl)-N-methylpropanamide

HRID 1471677Notes

Reaction equation

HRID 1471677 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]([O:13]CC)=O.[C-:16]#[N:17].[Na+].CN>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]([NH:17][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 67982372Ethyl 3-(2-bromo-6-chlorophenyl)propanoate

Product 1

HCID 679825833-(2-bromo-6-chlorophenyl)-N-methylpropanamide

Procedure

Ethyl 3-(2-bromo-6-chlorophenyl)propanoate (Example 1f), 5.0 g, 17.1 mmol) and sodium cyanide (0.168 g, 3.43 mmol) were stirred in methanamine (8 M in ethanol, 30 mL, 240 mmol) at rt overnight. The solvent was evaporated, the residue was taken up in ethyl acetate and the mixture was washed with saturated aqueous sodium carbonate and brine. The organic phase was separated and the solvent was removed by rotary evaporation. The crude product was added to a silica gel column and was eluted with 0-100% ethyl acetate in heptane. The collected fractions were combined and the solvent was removed by rotary evaporation to give the title product. Yield 2.98 g, 63%. 1H NMR (500 MHz, CDCl3) δ ppm 2.40-2.47 (m, 2H) 2.85 (d, 3H) 3.28-3.35 (m, 2H) 5.44 (br. s., 1H) 7.02 (t, 1H) 7.33 (dd, Hz, 1H) 7.47 (dd, Hz, 1H). MS m/z 277.9 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. washthe mixture was washed with saturated aqueous sodium carbonate and brine
  3. customThe organic phase was separated
  4. customthe solvent was removed by rotary evaporation
  5. additionThe crude product was added to a silica gel column
  6. washwas eluted with 0-100% ethyl acetate in heptane
  7. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-7a722d3e224c494fb66e05f61f821503
Source dataset
uspto-grants-2015_04
Patent number
US09012457B2

Reaction notes

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