HCID 21270205, compound → HCID 21270170, compound

HRID 1194475Notes

Reaction equation

HRID 1194475 reaction equation
[OH:1][C:2]1[C:3]([OH:22])=[CH:4][C:5]2[O:10][CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1>O1CCOCC1.C(O)C.[Ni]>[OH:1][C:2]1[C:3]([OH:22])=[CH:4][C:5]2[O:10][CH:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=3)[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

5

Reactant 1

HCID 21270205HCID 21270205, compound

Product 1

HCID 21270170HCID 21270170, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

6,7-Dihydroxy-3-(4-nitrophenyl)-4H-1-benzopyran-4-one [cp. J. Inst. Chem. (Calcutta) 43, 234 (1971)] (1 g) is dissolved in 250 ml of a mixture of dioxan and ethanol 1:1. Raney nickel (0.45 g) is added and the mixture is hydrogenated for 18 h at room temperature, then filtered. The solution is evaporated under vacuum to about one third of its original volume until a precipitate occurs which is filtered and crystallized in dioxan to give 6,7-dihydroxy-3-(4-aminophenyl)-4H-1-benzopyran-4-one, m.p. 305°-306°.

Workup

  1. filtrationfiltered
  2. customThe solution is evaporated under vacuum to about one third of its original volume until a precipitate
  3. filtrationis filtered
  4. customcrystallized in dioxan

Sources & evidence

ORD record
ord-4e5885772e1d4df9b8455b774eee1f25
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

Loading…