Ammonium formate → Ethyl 8-aminoquinoline-3-carboxylate

HRID 1416941Notes

Reaction equation

HRID 1416941 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[C:15]2[C:10](=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>[Pd].C(O)C>[CH2:22]([O:21][C:19]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:6]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11196760Ethyl 4-chloro-8-nitroquinoline-3-carboxylate

Product 1

HCID 21250128Ethyl 8-aminoquinoline-3-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate was added to a vigorously stirred mixture of 4-chloro-3-ethoxycarbonyl-8-nitro-quinoline (5.6 g), ethanol (1000 ml) and 10% palladium on carbon catalyst (2 g). The mixture was stirred at ambient temperature for 1 hour, filtered through a pad of celite and the pad washed with dichloromethane. The combined filtrate and washings were evaporated to dryness. The residue so obtained was purified by flash chromatography on silica using chloroform as eluant to give 3-ethoxycarbonyl-8-amino-quinoline in 58% yield, mp 94-96° C.

Workup

  1. filtrationfiltered through a pad of celite
  2. washthe pad washed with dichloromethane
  3. customThe combined filtrate and washings were evaporated to dryness
  4. customThe residue so obtained
  5. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-7a1ce72d16c0489c89aba36e3aff8d0b
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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