Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate → Methyl 7-amino-2,3-dihydro-1,4-benzodioxin-6-carboxylate

HRID 596604Notes

Reaction equation

HRID 596604 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][C:7]2[O:13][CH2:14][CH2:15][O:16][C:6]=2[CH:5]=1>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([NH2:10])=[CH:8][C:7]2[O:13][CH2:14][CH2:15][O:16][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 10537941Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

Product 1

HCID 3146109Methyl 7-amino-2,3-dihydro-1,4-benzodioxin-6-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 6.0 g. of 6-nitro-3,4-ethylenedioxybenzoic acid methyl ester, 150 mg. of 5% palladium on charcoal and 20 mls. of glacial acetic acid is hydrogenated under an initial hydrogen pressure of 30-40 p.s.i. and without external heating. After four hours the reaction mixture is filtered diluted with 80 ml. of ice water, stirred up one half hour and the resulting precipitate filtered off, water washed and dried to obtain 6-amino-3,4-ethylenedioxybenzoic acid methyl ester, m.p. 73°-77° C.

Workup

  1. additionA mixture of 6.0 g
  2. filtrationAfter four hours the reaction mixture is filtered
  3. additiondiluted with 80 ml
  4. filtrationthe resulting precipitate filtered off
  5. washwater washed
  6. customdried

Sources & evidence

ORD record
ord-f940b815c6d64281b0e557a1548047c4
Source dataset
uspto-grants-1977_03
Patent number
US04011323

Reaction notes

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