Sodium Hydroxide → HCID 13064663, compound

HRID 2244350Notes

Reaction equation

HRID 2244350 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH:11][CH:12]([CH3:14])[CH3:13].[OH-].[Na+]>CO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([NH:11][CH:12]([CH3:14])[CH3:13])=[C:4]([CH:9]=1)[C:3]([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17606704HCID 17606704, compound

Product 1

HCID 13064663HCID 13064663, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 480 mg of 5-chloro-2-isopropylamino-benzoic acid methyl ester in methanol (5 ml) were added 3.16 ml of a 1N NaOH solution and the mixture was stirred for 4 d at RT. Then the reaction mixture was concentrated in vacuo and the remaining residue dissolved in water. The resulting solution was washed with ethyl acetate and then the pH was adjusted to 1 with 1N HCl solution and the mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated to give the title compound as an off-white solid (429 mg, 95%). NMR (CDCl3, 300 MHz): δ 1.27 (d, J=6.3 Hz, 6H), 3.70 (sept, J=6.3 Hz, 1H), 6.65 (d, J=9.1 Hz, 1H), 7.31 (dd, J=9.1 and 2.7 Hz, 1H), 7.92 (d, J=2.7 Hz, 1H).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. dissolutionthe remaining residue dissolved in water
  3. washThe resulting solution was washed with ethyl acetate
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e544810b49648589a5d942c77b69278
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

Loading…