Hydrazine → HCID 178497541, compound

HRID 1978194Notes

Reaction equation

HRID 1978194 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=[CH:12][N:13](C)C)=[CH:6][C:5]=1[Cl:16].[NH2:18]N>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][NH:13][N:18]=2)=[CH:6][C:5]=1[Cl:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 545013412-Chloro-4-(3-dimethylamino-2-propen-1-yl)-benzoic acid methyl ester

Product 1

HCID 178497541HCID 178497541, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-chloro-4-(3-dimethylamino-2-propen-1-yl)-benzoic acid methyl ester of Step B (6.13 g, 22.9 mmol) and anhydrous hydrazine (1.44 mL, 45.8 mmol) in 15 mL of glacial acetic acid was heated at 90° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated and the residual solid triturated with diethyl ether-hexane to give the title compound (5.1 g) as an orange solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residual solid triturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-1fa6c5236a814e8faa386d789bf0bc95
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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