Sodium Hydroxide → HCID 67443041, compound

HRID 1801342Notes

Reaction equation

HRID 1801342 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O-:22])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:23]([O-])=O.[OH-].[Na+]>CO>[NH2:23][C:3]1[CH:4]=[C:5]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67441230HCID 67441230, compound

Product 1

HCID 67443041HCID 67443041, compoundYield 293.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (0.5 g, 0.52 mmol) in methanol (10 mL) and 1 M aqueous sodium hydroxide solution (26 mL, 26 mmol) was heated to reflux for 3 h. LC-MS showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 1 M hydrochloric acid solution to pH=6. The precipitated white solid was collected by filtration and washed with water, dried in vacuo to afford 0.48 g of 2-(3-amino-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid in quantitative yield.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. filtrationThe precipitated white solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a4e96e61d5374ef3b70fd7b259f092db
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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