HCID 12767926, compound → HCID 12767927, compound

HRID 1902244Notes

Reaction equation

HRID 1902244 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16](=[O:17])[C:10]3([CH2:14][CH2:13][O:12][C:11]3=[O:15])[S:9][C:8]=2[CH:18]=1)([O-])=[O:2]>C(OCC)(=O)C.C(O)(=O)C.[C].[Pd]>[OH:2][NH:1][C:4]1[CH:5]=[CH:6][C:7]2[C:16](=[O:17])[C:10]3([CH2:14][CH2:13][O:12][C:11]3=[O:15])[S:9][C:8]=2[CH:18]=1

Participants

5

Reactant 1

HCID 12767926HCID 12767926, compound

Product 1

HCID 12767927HCID 12767927, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 35 ml of ethyl acetate and 3.5 ml of acetic acid was dissolved 356.3 mg of 6-nitro-4',5'-dihydrospiro[benzo[b]thiophen-2(3H),3'(2'H)-furan]-3,2'-dione as obtained in Reference Example 7, and was subjected to catalytic reduction under atmospheric pressure at room temperature in the presence of 113.3 mg of 5% palladium carbon. After absorption of hydrogen stopped, the catalyst was filtered off, and the filtrate was evaporated to dryness under reduced pressure. Recrystallization of the residue from water-acetone (7:3) yielded yellow needles of 6-hydroxyamino-4',5'-dihydrospiro[benzo[b]thiophene-2(3H),3'(2'H)-furan]-3,2'-dione. Melting point: 184°-186° C.

Workup

  1. customas obtained in Reference Example 7
  2. customAfter absorption of hydrogen
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customRecrystallization of the residue from water-acetone (7:3)

Sources & evidence

ORD record
ord-3a2f3806437f42a5a95137842e0e651b
Source dataset
uspto-grants-1982_12
Patent number
US04362740

Reaction notes

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