(E)-4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-but-3-enoic acid methyl ester → 4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester

HRID 1669721Notes

Reaction equation

HRID 1669721 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4]/[CH:5]=[CH:6]/[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([NH:17][CH2:18][C:19]1[O:20][C:21]([CH3:24])=[CH:22][CH:23]=1)=[N:12]2.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][C:11]([NH:17][CH2:18][C:19]1[O:20][C:21]([CH3:24])=[CH:22][CH:23]=1)=[N:12]2

Participants

5

Reactant 2

HCID 67332240(E)-4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-but-3-enoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 442181534-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(E)-4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-but-3-enoic acid methyl ester (290 mg, 0.86 mmol) was dissolved in 45 mL ethanol. Palladium on charcoal (10%, 92 mg, 0.086 mmol) was added and the reaction mixture war hydrogenated with a hydrogen balloon overnight. The palladium was filtered off and the solvent was evaporated. The title compound was obtained as a brown oil (256 mg, 88%), MS: m/e=339.1 (M+H+).

Workup

  1. filtrationThe palladium was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-77f2a32d2f6c4147b56c27120259c6b6
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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