Sodium Hydroxide → HCID 58476151, compound

HRID 1801323Notes

Reaction equation

HRID 1801323 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([O:24]C)=[O:23])[CH:16]=3)[NH:11]2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].[OH-].[Na+]>CO>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]([CH3:21])([CH3:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:22]([OH:24])=[O:23])[CH:16]=3)[NH:11]2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67440751HCID 67440751, compound

Product 1

HCID 58476151HCID 58476151, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-carbamoylphenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxy late (84 mg, 0.25 mmol) in methanol (4.5 mL) and 1 M sodium hydroxide aqueous solution (3.2 mL, 3.2 mmol, 13.0 eq.) was heated to reflux for 30 min, LC-MS showed the reaction was complete and only the desired product formed. The solvent was concentrated in vacuo and the residue was dissolved in water and acidified with 1 M hydrochloric acid solution to pH=6. The white precipitated solid was collected by filtration and dried in vacuo to afford 50 mg of 2-(3-carbamoylphenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid. Yield: 62.1%. MS (ESI+APCI) M+1=325.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min

Sources & evidence

ORD record
ord-5149f1295a584d3fbcf23b650bfd1818
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…