Sodium Hydroxide → HCID 19919472, compound

HRID 1648324Notes

Reaction equation

HRID 1648324 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 4.0 N 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 4.0 N 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 4.0 N hydrochloric acid (3.3 mL)
  3. filtrationThe precipitate was filtered off
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-f48a66ae9cb84c79aa7a4c24207655e3
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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