Triethylamine → 6-Cyano-quinoline-3-carboxylic acid ethyl ester

HRID 333842Notes

Reaction equation

HRID 333842 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([C:17]#[N:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([C:17]#[N:18])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 12069372HCID 12069372, compound

Product 1

HCID 574213466-Cyano-quinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 4-chloro-6-cyanoquinoline-3-carboxylic acid ethyl ester [CAS Reg. No 403841-76-9] (5 g) in ethanol (30 ml) were added triethylamine (3.90 g) and Pd (5% on charcoal, 200 mg). The mixture was stirred under a hydrogen atmosphere for 3.5 h using a balloon. The catalyst was filtered off and the filtrate was concentrated. Since the reaction was not finished, the hydrogenation was repeated using the same conditions. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1) to give the title compound (2.1 g) as a colorless solid. MS (m/e)=227.2 [M+H+].

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>0:1)

Sources & evidence

ORD record
ord-a1d72c1fa7f2428a9efadad1ebde3ce3
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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