Hydrazine → 1,4-Naphthalenedione, 5-amino-2,3-dimethoxy-

HRID 414622Notes

Reaction equation

HRID 414622 reaction equation
[NH2:1]N.ClC1C=C(Cl)C=C[C:5]=1[O:6][C:7]1[C:8](=[O:30])[C:9]2[C:14]([C:15](=[O:26])[C:16]=1[O:17][C:18]1C=CC(Cl)=CC=1Cl)=[CH:13][C:12]([N+]([O-])=O)=[CH:11][CH:10]=2>[Pd].C(O)C>[CH3:5][O:6][C:7]1[C:8](=[O:30])[C:9]2[C:14]([C:15](=[O:26])[C:16]=1[O:17][CH3:18])=[C:13]([NH2:1])[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 23038373HCID 23038373, compound

Product 1

HCID 122506961,4-Naphthalenedione, 5-amino-2,3-dimethoxy-Yield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrazine (4.0 ml, 125 mmol of 97%) was added dropwise, over a 2 hour period, to a stirred mixture of the captioned compound of Preparation 2 (19.9 g, 75.6 mmol), 5% palladium on carbon (10 g) and ethanol (750 ml) in a nitrogen atmosphere. The catalyst was filtered off through a celite pad that was washed with hot ethanol (2×300 ml). The combined filtrate and washings were concentrated to dryness in vacuo and the residue recrystallized from water:ethanol (1.5:1) giving 14.6 g of 2,3-dimethoxy-5-amino-1,4-naphthoquinone, mp 116°-117°.

Workup

  1. filtrationThe catalyst was filtered off through a celite pad that
  2. washwas washed with hot ethanol (2×300 ml)
  3. concentrationThe combined filtrate and washings were concentrated to dryness in vacuo
  4. customthe residue recrystallized from water:ethanol (1.5:1)

Sources & evidence

ORD record
ord-f1756096266e4e2e912516f64c9bf6cd
Source dataset
uspto-grants-1988_12
Patent number
US04792556

Reaction notes

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