Formic Acid → N-[5-chloro-2-(methylphenylamino)phenyl]formamide

HRID 16185Notes

Reaction equation

HRID 16185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[CH:17](O)=[O:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([NH:16][CH:17]=[O:18])[CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 167750454-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine

Product 1

HCID 59343244N-[5-chloro-2-(methylphenylamino)phenyl]formamideYield 100%

Procedure

4-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine (9.3 g, 40.1 mmol) was dissolved in formic acid (60 mL) and heated to reflux. After 2 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (500 mL) and washed with aq. NaHCO3 (5%, 500 mL). The organic layer was dried, filtered and concentrated under reduced pressure. The residual oil was chromatographed over silica (cyclohexane/CH2Cl2, 9/1, v/v) to give pure title compound (10.4 g, 100% yield). Data: Rf 0.25 (heptane/ethyl acetate, 3/1, v/v). (m/z)=261 (M+H)+.

Workup

  1. temperatureheated to reflux
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  4. washwashed with aq. NaHCO3 (5%, 500 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residual oil was chromatographed over silica (cyclohexane/CH2Cl2, 9/1

Sources & evidence

ORD record
ord-fdb3264cf4f4410d81b567b228a0ecdb
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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