Ethanol → N-(3-chloro-4-fluorophenyl)-4-methylbenzamide

HRID 1968937Notes

Reaction equation

HRID 1968937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+]([O-])=O)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(O)C.[Cl-].[NH4+].C(=O)([O-])[O-].[K+].[K+]>[Fe].O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 710855N-(3-chloro-4-fluorophenyl)-4-methyl-3-nitrobenzamide

Product 1

HCID 710613N-(3-chloro-4-fluorophenyl)-4-methylbenzamideYield 117.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

0.7 g of the product of Step 1 was added into 80 ml of ethanol:water (v/v=31), then 1.0 g iron powder and 0.4 g ammonium chloride. After addition, the reaction mixture was heated to 70° C. and reacted for 30 min. The completion of reaction was indicated by TLC. The reaction mixture was filtered, and the filter cake was washed with hot ethanol repeatedly. Then the filtrate was concentrated under reduced pressure to give a white solid. Then 20 ml potassium carbonate solution (10%) was added into the solid. The mixture was stirred, left to stand, filtered, and dried to give a light yellow solid (0.7 g).

Workup

  1. additionAfter addition
  2. customreacted for 30 min
  3. customThe completion of reaction
  4. filtrationThe reaction mixture was filtered
  5. washthe filter cake was washed with hot ethanol repeatedly
  6. concentrationThen the filtrate was concentrated under reduced pressure
  7. customto give a white solid
  8. waitleft
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-ea0c9244a5254fab920761172bc75e8c
Source dataset
uspto-grants-2013_04
Patent number
US08426446B2

Reaction notes

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