Hydrochloric Acid → 6-Cyanoquinoline-3-carboxylic acid

HRID 1097944Notes

Reaction equation

HRID 1097944 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=2)=[O:5])C.[Li+].[OH-].Cl>O1CCCC1.C(O)C>[C:16]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15]2)#[N:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 574213466-Cyano-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 574213476-Cyanoquinoline-3-carboxylic acidYield 107%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-cyano-quinoline-3-carboxylic acid ethyl ester (1.28 g) in tetrahydrofuran (6 ml) and ethanol (6 ml) was added a 1M aqueous LiOH solution (6.79 ml) at 0° C. The mixture was stirred at 0° C. for 1.5 h, then the mixture was acidified with 1M aqueous HCl. The precipitate was filtered off, washed with water and a small amount of ether and dried to give the crude title compound (1.2 g) as an off-white solid that was used in the next step without further purification. MS (m/e, ISP neg. ion)=197.2 [M−H+].

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. dry with materiala small amount of ether and dried

Sources & evidence

ORD record
ord-2843742c157140938545cf2d9a982de0
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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