1,2-Dichloroethane → N'-acetyl-4-bromo-2-methoxybenzohydrazide

HRID 2035678Notes

Reaction equation

HRID 2035678 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH3:12])[CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:27]([NH:30][NH2:31])(=[O:29])[CH3:28]>CN(C=O)C.CCOC(C)=O>[C:27]([NH:30][NH:31][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[O:11][CH3:12])(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 134507554-Bromo-2-methoxybenzoic acid

Product 1

HCID 66684712N'-acetyl-4-bromo-2-methoxybenzohydrazide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-2-methoxybenzoic acid (950.7 mg, 4.11 mmol) in 8 ml of DMF was treated sequentially with EDC (1183 mg, 6.17 mmol) and HOBT (945 mg, 6.17 mmol) and stirred at room temperature for 10 minutes. The reaction was then treated with acetic hydrazide (366 mg, 4.94 mmol) and stirred at room temperature overnight. The reaction was dissolved in EtOAc and washed sequentially with saturated bicarbonate solution and brine. The aqueous washes were extracted once with EtOAc. Organics were combined, dried over sodium sulfate, and concentrated under reduced pressure to a white solid (1.37 g crude).

Workup

  1. stirringstirred at room temperature overnight
  2. washwashed sequentially with saturated bicarbonate solution and brine
  3. extractionThe aqueous washes were extracted once with EtOAc
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure to a white solid (1.37 g crude)

Sources & evidence

ORD record
ord-99f8cedac2504e34bad35643b1c11511
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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