Hydrazine → HCID 178421585, compound

HRID 1489777Notes

Reaction equation

HRID 1489777 reaction equation
[CH3:1][C:2]1[C:3]([C:19]([O:21]CC)=O)=[N:4][C:5]2[C:6]=1[C:7]([CH3:18])=[C:8]1[C:16]([CH:17]=2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]2)=[N:9]1.[NH2:24][NH2:25]>>[CH3:1][C:2]1[C:3]([C:19]([NH:24][NH2:25])=[O:21])=[N:4][C:5]2[C:6]=1[C:7]([CH3:18])=[CH:8][C:16]1[C:17]=2[N:9]=[C:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2

Participants

3

Reactant 2

HCID 9321HydrazineHCID 19367650HCID 19367650, compound

Product 1

HCID 178421585HCID 178421585, compound

Conditions

Temperature
120 °C

Procedure

Ethyl 3,4-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate (500 mg) and 95% hydrazine (5 cm3) were stirred and heated at 120° C. for 6 h in a Readi-Vial. The mixture was allowed to stand overnight, cooled in ice and filtered. The resulting yellow solid was washed carefully with water and dried. Yield of title compound 350 mg (73%), no sharp m.p. but decomposes at 285° C. (Found: C, 69;19; H, 5.57; N, 19.38. Calc. for C17H16N4O. 0.1H2O requires C, 69.42; H, 5.55; N, 19.05%); δH [2H6 ]-DMSO) 10.80 (1H, s, exchangeable, NH), 10.55 (1H, s, exchangeable, NH), 9.20 (1H, s, exchangeable, NH), 8.06 (1H, d, J7.5 9-H), 7.81 (1H, s, 10-H), 7.42-7.28 (2H, m, 6-H and 7-H) 7.12-7.01 (1H, m, 8-H, 4.5 (2H, br, s, exchangeable, NH2), and 2.4 and 2.3 (2×s, 4-CH3 and 3-CH3), m/z 293 (M+1)+, FAB)].

Workup

  1. temperaturecooled in ice
  2. filtrationfiltered
  3. washThe resulting yellow solid was washed carefully with water
  4. customdried
  5. customdecomposes at 285° C.

Sources & evidence

ORD record
ord-cf60d5767bed4c959a26b8ce32edd04b
Source dataset
uspto-grants-1997_10
Patent number
US05679694

Reaction notes

Loading…