Acetonitrile → N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284611Notes

Reaction equation

HRID 1284611 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19].[C:20](=O)([O-])[O-].[K+].[K+].[C:26](#N)[CH3:27]>CN(C)C=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:26]([CH3:27])[CH3:20])=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[C:12]2[CH2:15][CH2:16][CH2:17][CH2:18][C:11]=2[C:10]1=[O:19]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 13519181N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

Product 1

HCID 13556385N-(2-Fluoro-5-isopropoxyphenyl)-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(2-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (VI) (9 g), n-amyl chloroacetate (8 g) and potassium carbonate (6.7 g) were dissolved in a mixture of acetonitrile (50 ml) and dimethylformamide (10 ml), and the resultant mixture was heated under reflux for 6 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The solvent was removed under reduced pressure to give 12 g of N-(2-fluoro-5-n-amyloxycarbonylmethoxyphenyl)-3,4,5,6-tetrahydrophthalimide (II: R=n-amyloxycarbonylmethyl). nD25 1.5218.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-70a1edfb86d94ee0b68fa14aae86309c
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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