Acetic Acid → HCID 19711231, compound

HRID 724871Notes

Reaction equation

HRID 724871 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:3]=1[N+:16]([O-])=O.C(O)(=O)C>C(O)C.[Pd]>[NH2:16][C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]=2[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19711229HCID 19711229, compound

Product 1

HCID 19711231HCID 19711231, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred suspension of methyl 8-amino-7-nitro-1,4-benzodioxan-5-carboxylate (300 mg, 0.0012 mole) in ethanol (30 ml) together with glacial acetic acid (5 ml) was hydrogenareal over 10% Pd-C (100 mg) at atmospheric pressure and temperature for 5 h. The catalyst was filtered off and the filtrate concentrated in vacuo. The residue was basified with concentrated potassium carbonate solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford methyl 7,8-diamino-1,4-benzodioxan-5-carboxylate as a beige solid (240 mg, 92%). 1H NMR (CDCl3) δ:6.91(s,1 H), 4.21(s,4 H), 3.96(br s.2 H), 3.74(s,3 H), 3.0(br s,2 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cffc758317bd4280ba76d75e86c2e51f
Source dataset
uspto-grants-1998_01
Patent number
US05705509

Reaction notes

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