Hydrochloric Acid → N-(2-chloro-3,5-dimethoxyphenyl)acetamide

HRID 58175

Reaction equation

HRID 58175 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Cl.[Cl:16]([O-])(=O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O>[Cl:16][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 516902Sodium ChlorateHCID 702039N-(3,5-dimethoxyphenyl)acetamide

Product 1

HCID 56594868N-(2-chloro-3,5-dimethoxyphenyl)acetamideYield 71.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(3,5-dimethoxy-phenyl)-acetamide (5 g, 25.64 mmol) in acetic acid (17 mL) was added 32% aqueous hydrochloric acid solution (14 mL), followed by a solution of sodium chlorate (1.16 g, 11 mmol) in water (1.5 mL) at 0° C. The resulting reaction mixture was stirred for 30 min. at 0° C. Thereafter reaction mixture was poured into ice water and made it basic with K2CO3 powder. The precipitate was filtered off and washed with water. The residue was purified by silica gel column chromatography (Hexane/EtOAc, 88:12) to afford the title compound (1.8 g, 31% of yield) as a white solid. 1HNMR (DMSO-d6, 300 MHz): δ 9.36 (s, 1H), 7.03 (d, 1H), 6.53 (d, 1H), 3.84 (s, 3H), 3.74 (s, 3H), 2.08 (s, 3H); MS (ESI): 230.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customThereafter reaction mixture
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe residue was purified by silica gel column chromatography (Hexane/EtOAc, 88:12)

Sources & evidence

ORD record
ord-eab1288e2d1b4eb699d8367c81799a3c
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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