Lithium Hydroxide → HCID 53692096, compound

HRID 906119Notes

Reaction equation

HRID 906119 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+]>CO>[CH3:1][C:2]1[C:11]([NH:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 630918011149388-16-8

Product 1

HCID 53692096HCID 53692096, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To methyl 2-methyl-3-(methylamino)benzoate (125 mg, 0.698 mmol) in methanol (7 ml) was added 2M aqueous lithium hydroxide (1.8 ml, 3.63 mmol), and the solution was stirred at 25° C. for 3 h, at which point the volume was reduced by rotary evaporation. The aqueous mixture was diluted with water (3 ml) and the pH adjusted to 5 with 1 N hydrochloric acid. The resultant precipitate was collected by filtration and dried in vacuo to afford (50 mg, 42%) of 2-methyl-3-(methylamino)benzoic acid. MS (EI) for C9H11NO2: 166 (MH+).

Workup

  1. customwas reduced by rotary evaporation
  2. additionThe aqueous mixture was diluted with water (3 ml)
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5ff3a565181445e087b10699a7db3264
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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