6-[3-(Imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyril → 6-[3-(Imidazol-1-yl)prop-1-en-1-yl]-3,4-dihydrocarbostyril

HRID 414563Notes

Reaction equation

HRID 414563 reaction equation
[N:1]1([CH2:6][C:7]#[C:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H]>[Pd].N1C=CC=CC=1>[N:1]1([CH2:6][CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 143732826-[3-(Imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyrilHCID 178418361HCID 178418361, compound

Product 1

HCID 537011596-[3-(Imidazol-1-yl)prop-1-en-1-yl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent2×

Procedure

A suspension of 75 mg of 5% palladium on barium sulfate catalyst in 8 ml of pyridine was stirred under hydrogen for 15 minutes. A solution of 502 mg of 6-[3-(imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyril in 3 ml of pyridine was added and the mixture stirred under hydrogen until the theoretical volume of hydrogen had been absorbed. The reaction mixture was filtered and the solvent removed from the filtrate under reduced pressure to give a residue which was recrystallized from a mixture of methanol and ethyl acetate to give 6-[3-(imidazol-1-yl)prop-1-en-1-yl]-3,4-dihydrocarbostyril, m.p. 158°-160° C.

Workup

  1. customhad been absorbed
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed from the filtrate under reduced pressure
  4. customto give a residue which
  5. customwas recrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-85da0d4e99df4c21991e2e599b1e78f7
Source dataset
uspto-grants-1988_12
Patent number
US04792561

Reaction notes

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