Hydrazine hydrate (1:1) → HCID 178489133, compound

HRID 735422Notes

Reaction equation

HRID 735422 reaction equation
F[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O.O.[NH2:20][NH2:21]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[C:3]3[C:2](=[C:7]([CH3:8])[CH:6]=[CH:5][CH:4]=3)[NH:21][N:20]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67021114(2-Fluoro-3-methylphenyl)(4-methoxyphenyl)methanone

Product 1

HCID 178489133HCID 178489133, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of (2-fluoro-3-methylphenyl)-(4-methoxy-phenyl)-methanone (3.6 g, 14.7 mmol), hydrazine hydrate (4.3 mL, 140 mmol) and DMAP (1.8 g, 14.7 mmol) in pyridine was heated at 100 C for 24-48 hrs. The cooled reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The resulting residue was purified by flash chromatography to give the product (1.7 g) as a yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dc190388c10c4b97b23ed54bfa21336b
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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