HCID 19858077, compound → HCID 19858079, compound

HRID 2073393Notes

Reaction equation

HRID 2073393 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)=[C:12]([N+:22]([O-])=O)[CH:11]=3>[Pd].C(O)(=O)C>[NH2:22][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[CH2:16][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:3]1[C:2]([CH3:1])([CH3:25])[C:6](=[O:7])[O:5][C:4]=1[CH:8]=[CH:9]2

Participants

4

Reactant 1

HCID 19858077HCID 19858077, compound

Product 1

HCID 19858079HCID 19858079, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1,1-dimethyl-7-nitro-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone (0.035 g), glacial acetic acid (2 ml) and 10% palladium-on-carbon (0.01 g) was stirred under an atmosphere of hydrogen at room temperature and atmospheric pressure for 2 h. The mixture was filtered, the filtrate was evaporated to dryness under reduced pressure, and the residue was partitioned between ethyl acetate and equeous sodium hydrogen carbonate solution. The ethyl acetate phase was dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography using methanol:ethyl acetate, 1:99 v/v. as eluant, to give 7-amino-1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 160°-163°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and equeous sodium hydrogen carbonate solution
  4. dry with materialThe ethyl acetate phase was dried
  5. customevaporated to dryness under reduced pressure
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1575ea99c30f4333a86d6d7319eccae6
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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