5-Hydroxy-2-nitrobenzoic acid → Methyl 5-hydroxy-2-nitrobenzoate

HRID 1095009Notes

Reaction equation

HRID 1095009 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14](OC(=O)C1C=C(OCCOC)C(OCCOC)=CC=1N)C.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>CO>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 118825-Hydroxy-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

Product 1

HCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

5-Hydroxy-2-nitro-benzoic acid (compound A′) (2.0 g) was dissolved in methanol (30 ml). Thionyl chloride (3.0 ml) was added dropwise to the solution on an ice bath, and the mixture was then stirred at 75° C. for 96 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 5-hydroxy-2-nitro-benzoic acid methyl ester (2.2 g, crude yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. extractionwas then subjected to separatory extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationwas then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-db9efb25a24c4dda9927ce199ee8c24e
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

Loading…