Hydrazine hydrate (1:1) → 1-(5-(2-Fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanamine

HRID 709616Notes

Reaction equation

HRID 709616 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][N:22]2C(=O)C3C(=CC=CC=3)C2=O)=[N:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:20])[CH3:19].O.NN>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][NH2:22])=[N:14][C:15]=1[O:16][CH2:17][CH:18]([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1177602692-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1177599721-(5-(2-Fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanamineYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methyl)-1H-isoindole-1,3(2H)-dione (228 mg) in ethanol (3.0 ml) was added hydrazine monohydrate (3.0 mL), and the mixture was stirred at room temperature for 20 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (152 mg) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8625c075deb244989bf707572c2ba0fa
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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