Sodium Hydroxide → HCID 22621090, compound

HRID 841160Notes

Reaction equation

HRID 841160 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, 44.6ml) 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-e52ba486c8ed4ef7b54c0ea7cdaaa7f1
Source dataset
uspto-grants-2002_04
Patent number
US06369270B1

Reaction notes

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