Formamide → HCID 178517949, compound

HRID 27766Notes

Reaction equation

HRID 27766 reaction equation
CO[C:3]([C:5]1[C:6]([NH2:14])=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4].[CH:15]([NH2:17])=O>>[NH:12]1[C:13]2=[C:5]3[C:6]([CH:7]=[CH:8][C:9]2=[CH:10][NH:11]1)=[N:14][CH:15]=[N:17][C:3]3=[O:4]

Participants

3

Reactant 2

HCID 713FormamideHCID 12637848Methyl 6-amino-1H-indazole-7-carboxylate2×

Product 1

HCID 178517949HCID 178517949, compound

Procedure

6-Amino-1H-indazole-7-carboxylic acid methyl ester (formula 14, obtained according to Example IV) (1.35 g, 7.0 m-mol) was heated with formamide (4.2 ml) at 140° for a period of 4 hours and again at 180° for a period of 1.5 hours. The product that formed on cooling was collected and washed with a small amount of cold water to yield 555 mg of the formula 2 target compound. Additional amounts of the target compound were obtained by working-up the mother liquor. The cumulative product yield was 965 mg (74%), m.p. 325°-327° (decomp.); ir (KBr): 1570, 1620, 1685 cm-1 (aromatic, C=C, C=N, CO); pmr (DMSO-d6): δ 7.45 and 8.22 (2 d, 2, J=9 Hz, H4 and H5), 8.30 and 8.32 (2s, 2, H3 and H7), 13.44 (broad m, 2, D2O-exchangeable N1 --H and N8 --H); ms (70 eV): m/e 186 (100%, M+), 158 (16%, M+--CO).

Workup

  1. customThe product that formed
  2. temperatureon cooling
  3. customwas collected
  4. washwashed with a small amount of cold water

Sources & evidence

ORD record
ord-5c6e573c6dfb4c4fbfc2930e08067121
Source dataset
uspto-grants-1980_09
Patent number
US04223143

Reaction notes

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