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

HRID 1579242Notes

Reaction equation

HRID 1579242 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 for up to 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. filtrationthe 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-4ca80b449de04829b99e2a9ebc4ed06c
Source dataset
uspto-grants-1976_01
Patent number
US03931179

Reaction notes

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