Ammonium formate → 8-(3-hydroxy-3-methyl-butyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970054Notes

Reaction equation

HRID 1970054 reaction equation
[OH:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4][C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[CH:18][C:8]=3[C:7]=2[CH:6]=1.[CH2:21]([C:23]([O-:25])=[O:24])[CH3:22].C([O-])=O.[NH4+]>[Pd].C(O)C>[OH:1][C:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[NH:11][C:10](=[O:15])[C:9]3[NH:16][CH:17]=[CH:18][C:8]=3[C:7]=2[CH:6]=1.[CH2:21]([C:23]([O-:25])=[O:24])[CH3:22]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 866275568-(3-hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275608-(3-hydroxy-3-methyl-butyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 10.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 47 mg (0.14 mmol) of 8-(3-hydroxy-3-methyl-but-1-ynyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate, 164 mg (2.6 mmol) of ammonium formate and 5 mg of palladium on charcoal in 10 ml of ethanol is refluxed for 8 hours. The solution is filtered on celite and then evaporated. Water is added and the product is extracted twice with ethyl acetate. The organic phases are dried over magnesium sulfate, filtered and evaporated to give 5 mg (10%) of 8-(3-hydroxy-3-methyl-butyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a colourless oil.

Workup

  1. temperatureis refluxed for 8 hours
  2. filtrationThe solution is filtered on celite
  3. customevaporated
  4. additionWater is added
  5. extractionthe product is extracted twice with ethyl acetate
  6. dry with materialThe organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-71288c6909644284851c4706873e35b7
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…