Water → HCID 18183110, compound

HRID 430659Notes

Reaction equation

HRID 430659 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[C:5]([C:13](=O)[C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:4]=1.O.[NH2:25][NH2:26].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[CH2:9][C:10](=[O:11])[NH:25][N:26]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 18183137HCID 18183137, compound

Product 1

HCID 18183110HCID 18183110, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.8 g of 2-(4-methoxy-2-(4-nitrobenzoyl)phenyl)acetic acid is mixed in 200 ml of tetrahydrofuran with 2.3 ml of 80% hydrazine hydrate and stirred for 6 hours at room temperature. After standing overnight, it is mixed with 50 ml of water, and the tetrahydrofuran is drawn off in a rotary evaporator. The precipitated 2-(4-methoxy-2-(4-nitrobenzoyl)phenyl)acetic acid hydrazide (4.9 g) is suctioned off and stirred in 37 ml of glacial acetic acid at room temperature for 2 hours. It is diluted with 37 ml of water and suctioned off. 4.37 g of 8-methoxy-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepin-4-one with a melting point of 282° C. is obtained.

Workup

  1. waitAfter standing overnight
  2. customthe tetrahydrofuran is drawn off in a rotary evaporator
  3. stirringstirred in 37 ml of glacial acetic acid at room temperature for 2 hours
  4. additionIt is diluted with 37 ml of water

Sources & evidence

ORD record
ord-e65c0b70a94c423c9fe7105da3cc4cca
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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