Hydrazine hydrate (1:1) → 1-(2,4-dimethoxybenzyl)-3-hydrazinobenzo[f]quinoxalin-2(1H)-one

HRID 744022Notes

Reaction equation

HRID 744022 reaction equation
Cl[C:2]1[C:11](=[O:12])[N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])[C:9]2[C:8]3[CH:24]=[CH:25][CH:26]=[CH:27][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.O.[NH2:29][NH2:30]>ClCCl>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][N:10]1[C:9]2[C:8]3[CH:24]=[CH:25][CH:26]=[CH:27][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=[C:2]([NH:29][NH2:30])[C:11]1=[O:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 194214273-chloro-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one

Product 1

HCID 194214421-(2,4-dimethoxybenzyl)-3-hydrazinobenzo[f]quinoxalin-2(1H)-oneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloro-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one (900 mg, 2.4 mmol) and hydrazine hydrate (250 μl, 5.1 mmol) in dichloromethane (70 ml) was stirred at room temperature. After 48 h the mixture was evaporated to dryness. The residue was triturated with ice/water, filtered and dried in vacuo to give 800 mg (85%) of the title compound. M.p. 182°-183° C., 1H-NMR (CDCl3): δ 3.80 (s, 3H), 3.85 (s, 3H), 4,15 (br. s, 2H), 5.58 (s, 2H), 6.45 (dd, 1H), 6.58 (d, 1H), 7.05 (d, 1H), 7.40 (m, 3H), 7.70 (s, 2H), 7.85 (dd, 1H), 8.10 (d, 1H).

Workup

  1. customAfter 48 h the mixture was evaporated to dryness
  2. customThe residue was triturated with ice/water
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-edf606c43bda45c1b72254718860e67b
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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