Isopropanol → 2-Aminoquinoline-6-carboxylic acid

HRID 2376804Notes

Reaction equation

HRID 2376804 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH2:21])[CH:15]=[CH:14]2)=[O:10])C1C=CC=CC=1.CC(O)C.[OH-].[K+]>O>[NH2:21][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:9]([OH:10])=[O:8])[CH:12]=2)[N:17]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 11414765Benzyl 2-aminoquinoline-6-carboxylate

Product 1

HCID 220188622-Aminoquinoline-6-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-quinoline-6-carboxylic acid benzyl ester (15.63 g, 0.0562 moles), 2-propanol (235 mL), water (15.6 mL) and potassium hydroxide (6.3 g, 0.112 moles) was heated to reflux, 80° C. to 85° C., for 2 to 4 hours. The reaction mixture was then cooled to 20° C. to 25° C., vacuum concentrated (volume of 160 mL) and granulated at 20° C. to 25° C. for 8 to 16 hours. The product was isolated by filtration (12.08 g, 0.0534 moles, 95% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux, 80° C. to 85° C., for 2 to 4 hours
  3. temperatureThe reaction mixture was then cooled to 20° C. to 25° C.
  4. concentrationvacuum concentrated (volume of 160 mL)
  5. customThe product was isolated by filtration (12.08 g, 0.0534 moles, 95% yield)

Sources & evidence

ORD record
ord-32ed8750af4e4fad89b837ac98354478
Source dataset
uspto-grants-2008_12
Patent number
US07468378B2

Reaction notes

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