m-Chlorophenylhydrazine hydrochloride → HCID 66765124, compound

HRID 1466780Notes

Reaction equation

HRID 1466780 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7](=O)[CH3:8].Cl.[Cl:14][C:15]1[CH:16]=[C:17]([NH:21]N)[CH:18]=[CH:19][CH:20]=1>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][C:6]1[C:18]2[C:17](=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=2)[NH:21][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 52106499HCID 52106499, compound

Product 1

HCID 66765124HCID 66765124, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Bromo-phenoxy)-propan-2-one (5.95 g, 26 mmol) and 3-chlorophenylhydrazine hydrochloride (4.65 g, 26 mmol) were combined in ACN (100 mL) and the reaction was heated to reflux for 1 hour. After cooling the reaction was worked-up using standard procedures then purified using silica gel chromatography to give a 3:4 mixture of separable regioisomers of which the minor component was the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling the reaction
  4. customthen purified
  5. customto give
  6. additiona 3:4 mixture of separable regioisomers of which the minor component

Sources & evidence

ORD record
ord-23929a12498443c4978661de1bb1387b
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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