Sodium Hydroxide → HCID 22621090, compound

HRID 1953115Notes

Reaction equation

HRID 1953115 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-methylethoxycarbonylamino)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-eb4fe631f8934387bd76e020b287bc5f
Source dataset
uspto-grants-2000_09
Patent number
US06114538

Reaction notes

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