Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate → 5-Methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1274940Notes

Reaction equation

HRID 1274940 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([O:18]C)=[O:17])[CH2:8]2>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([OH:18])=[O:17])[CH2:8]2

Participants

4

Reactant 1

HCID 18622485Methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 186225095-Methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylate (1.9 g, 7.1 mmol) in methanol (20 mL) and 2 M NaOH (10 mL) was refluxed for 1.5 h and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate and acidified. The organic phase was separated and dried and evaporated in vacuo to afford 1.7 g (95% yield) of crystals: mp (after recrystallization in diisopropyl ether/ethanol) 189-190° C.; EIMS (70 eV) m/z (relative intensity) 251 (30, M+).

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customthe solvent was evaporated in vacuo
  3. customThe organic phase was separated
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-30a2f70ab2c942b3b0918bf442675fa3
Source dataset
uspto-grants-2000_12
Patent number
US06159972

Reaction notes

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