Sodium Hydroxide → HCID 22621090, compound

HRID 610750Notes

Reaction equation

HRID 610750 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([N:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([O:9]C)=[O:8]>CO>[Cl:3][C:4]1[C:5]([N:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:21])=[C:6]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22620987HCID 22620987, compound

Product 1

HCID 22621090HCID 22621090, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (2M, 44.6 ml), was added dropwise during 5 minutes to a stirred solution of methyl 3,4-dichloro-2-(N-methyl-N-ethoxycarbonylamino)benzoate (9.1 g) in methanol. After 0.5 hours the methanol was evaporated, the residue diluted (water), washed (ether), acidified with potassium bisulphate and extracted (ethyl acetate). The extract was dried (magnesium sulphate) and evaporated to give 3,4-dichloro-2-(N-methyl-ethoxycarbonylamino)benzoic acid (9.38 g) as a brown oil, NMR 1.2(m,3H), 3.1(s,3H), 4.0(m,2H), 7.4(m,1H), 7.9(m,1H).

Workup

  1. customAfter 0.5 hours the methanol was evaporated
  2. additionthe residue diluted (water)
  3. washwashed (ether)
  4. extractionextracted (ethyl acetate)
  5. dry with materialThe extract was dried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-d774008efbaf44f4b18c244a52c21778
Source dataset
uspto-grants-1999_12
Patent number
US05998653

Reaction notes

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