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 1274923Notes

Reaction equation

HRID 1274923 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-d99bde37d7a444218055e02f5b9f2736
Source dataset
uspto-grants-2000_12
Patent number
US06159970

Reaction notes

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