Sodium Hydroxide → HCID 19919472, compound

HRID 327482Notes

Reaction equation

HRID 327482 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:14][C:13]2[C:8](=[C:9]([C:15]([O:17]C)=[O:16])[CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:19])[CH2:2][CH3:3].[OH-].[Na+]>CO>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][C:13]2[C:8](=[C:9]([C:15]([OH:17])=[O:16])[CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:19])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19919381Methyl 3-(dipropylamino)-1,2,3,4-tetrahydro-2-oxo-8-quinolinecarboxylate

Product 1

HCID 19919472HCID 19919472, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(dipropylamino)-1,2,3,4-tetrahydro-2-oxo-8-quinolinecarboxylate (1.0 g), methanol (15 mL) and 4.0N sodium hydroxide solution (3.3 mL) was stirred at room temperature for 30 minutes. The methanol was removed and the residue was reconstituted in water (5 mL) and neutralized by addition of 4.0N hydrochloric acid (3.3 mL). The precipitate was filtered off, washed with water and air dried to give 0.67 g of 3-(dipropylamino)-1,2,3,4-tetrahydro-2-oxo-8-quinolinecarboxylic acid, mp 214°-217° C. Anal Calcd for C16H22N2O3 : C, 66.18; H, 7.64; N, 9.65. Found: C, 65.99; H, 7.67; N, 9.62.

Workup

  1. customThe methanol was removed
  2. additionneutralized by addition of 4.0N hydrochloric acid (3.3 mL)
  3. filtrationThe precipitate was filtered off
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-6a2c6634d02042f38618a25fece3ded0
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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