Formic Acid → HCID 13282176, compound

HRID 904812Notes

Reaction equation

HRID 904812 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH3:11][N:12]1[C:16]([NH2:17])=[C:15]2[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:14]2=[N:13]1>O>[CH3:11][N:12]1[C:16]([NH:17][CH:1]=[O:3])=[C:15]2[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:14]2=[N:13]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 13282157HCID 13282157, compound

Product 1

HCID 13282176HCID 13282176, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (200 mL) and 98% formic acid (10 mL) was heated at 50°-60° C. for 15 minutes. After cooling, 2-methyl-2H-benzofuro[3,2-c]pyrazol-3-amine (5.0 g, 27 mmol, described in Example 6) was added. After stirring overnight at room temperature, the mixture was poured on a mixture of ice and water and extracted with methylene chloride. The organic extract was dried and evaporated. The residue was chromatographed through silica gel using 5% EtOH--CH2Cl2 (v/v) and the eluates were evaporated. Trituration of the resulting residue with diethyl ether gave 3.0 g of N-(2-methyl-2H-benzofuro[3,2-c]pyrazol-3-yl)formamide: mp 184°-187° C.; IR (mineral oil) 3190 and 1670 cm-1 ; UV max (MeOH) 269 nm (ε=21100), 222 (19500) and shoulder at 291 and 215; NMR (DMSO-d6) δ3.85 (3H, s), 7.5 (4H, m), 8.4 (1H, s) and 10.4 (1H, br); and Anal. Calcd for C11H9N3O2 : C, 61.39% H, 4.21% N, 19.53% and Found: C, 61.17% H, 4.27% N, 19.37%.

Workup

  1. temperaturewas heated at 50°-60° C. for 15 minutes
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. customwas dried
  6. customevaporated
  7. customThe residue was chromatographed through silica gel using 5% EtOH
  8. customCH2Cl2 (v/v) and the eluates were evaporated

Sources & evidence

ORD record
ord-fb372a4674d2436081bb66d5ca1c0f45
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

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