1-Propanol → 6-Aminoquinoline-5-carboxylic acid

HRID 1725877Notes

Reaction equation

HRID 1725877 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]#N.[OH-:14].[Na+].C([OH:19])CC>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([OH:19])=[O:14]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 14798Sodium HydroxideHCID 15072406-Aminoquinoline-5-carbonitrile

Product 1

HCID 205642906-Aminoquinoline-5-carboxylic acid

Conditions

Temperature
100 °C

Procedure

A mixture of 6-amino-5-quinolinecarbonitrile (0.99 g, 5.9 mmol, prepared as described in Chem. Pharm. Bull., 1985, 33, 13260-1366) in 1-propanol (50 mL) was treated with 10 mL concentrated NaOH and heated to 100° C. for 18 hours. The mixture was concentrated, diluted with water, and washed twice with diethyl ether. The aqueous phase was acidified to pH 5 with 1M HCl and extracted with ethyl acetate in a continuous extractor. The organic extracts were dried (MgSO4), filtered, and concentrated to provide the desired product (0.55 g). MS (DCI) m/e 206 (M+NH4)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. washwashed twice with diethyl ether
  4. extractionextracted with ethyl acetate in a continuous extractor
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-480ce771e0d842ca970b6bc87388589a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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