Water → HCID 86676286, compound

HRID 869464Notes

Reaction equation

HRID 869464 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[C:6]([CH3:17])[C:5]([N+:18]([O-])=O)=[CH:4][CH:3]=1.ClC1C([N+]([O-])=O)=CC=C(C)C=1C(NC1C=CC=CC=1)=O.O>CCO>[NH2:18][C:5]1[C:6]([CH3:17])=[C:7]([C:2]([Cl:1])=[CH:3][CH:4]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 71227353HCID 71227353, compoundHCID 71232769HCID 71232769, compound

Product 1

HCID 86676286HCID 86676286, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 6-chloro-2-methyl-3-nitro-N-phenylbenzamide 9 and 2-chloro-6-methyl-3-nitro-N-phenylbenzamide I-9′ (33.6.8 g, 116 mmol, 1.0 eq) in EtOH (400 mL), SnCl22.H2O (105 g, 464 mmol, 4.0 eq) was added and the resulting mixture was stirred at reflux for 3 h. The reaction mixture was allowed to cool and concentrated in vacuo. The residue was poured into water (500 mL) and the mixture was extracted with ethyl acetate (5×500 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2-20% ethyl acetate-petroleum ether) to afford the regio-isomer, 3-amino-6-chloro-2-methyl-N-phenylbenzamide I-10. The remaining mixture of 3-amino-6-chloro-2-methyl-N-phenylbenzamide I-10 and 5-amino-6-chloro-2-methyl-N-phenylbenzamide I-10′ was collected separately. Compound I-10′ was obtained by further column chromatography purification.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. additionThe residue was poured into water (500 mL)
  5. extractionthe mixture was extracted with ethyl acetate (5×500 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel (2-20% ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-e4af8546d0904396a162822d8bccc3a9
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

Loading…