Formic Acid → HCID 5328451, compound

HRID 1716836Notes

Reaction equation

HRID 1716836 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])=[CH:6][CH:5]=1.[CH:19](O)=O>C(OC)(OC)OC>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:18])=[CH:9][CH:8]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]=[CH:19]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 68667054HCID 68667054, compound

Product 1

HCID 5328451HCID 5328451, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A stirred solution of give 4-(2-aminophenylamino)benzoic acid methyl ester (13 g, 0.054 mol) in trimethyl orthoformate was treated with formic acid (13 mL), heated at reflux temperature for 1 h, cooled to room temperature and concentrated in vacuo. The residual oil was purified by column chromatography (silica, CHCl3/MeOH 1%) to give the title compound in 90% yield, 1H NMR (400 MHz, CDCl3): 8.26-8.28 (m, 3H), 8.17 (s, 1H), 7.90 (bs, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.59 (m, 1H), 7.40 (m, 1H), 7.26 (s, 1H). 3.9 (s, 3H). LCMS (ESI+) 253 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 h
  3. concentrationconcentrated in vacuo
  4. customThe residual oil was purified by column chromatography (silica, CHCl3/MeOH 1%)

Sources & evidence

ORD record
ord-2b746ad33aa54a8783a950a99a4b35e3
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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