HCID 14673954, compound → HCID 14674144, compound

HRID 581032Notes

Reaction equation

HRID 581032 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][C:6]2[CH:8]=[C:9]([N+:13]([O-])=O)[C:10]([NH2:12])=[CH:11][C:5]=2[CH:4]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:22].[H][H]>C(O)C.[C].[Pd]>[CH3:1][C:2]1([CH3:23])[O:7][C:6]2[CH:8]=[C:9]([NH2:13])[C:10]([NH2:12])=[CH:11][C:5]=2[CH:4]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:22]

Participants

5

Reactant 2

HCID 14673954HCID 14673954, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14674144HCID 14674144, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.28 g (0.87 mmol) of 3,4-dihydro-2,2-dimethyl-3-hydroxy-4-(1-piperidinyl)-6-amino-7-nitro-2H-benzo[b]pyran was dissolved in 44.8 g of ethanol and hydrogen gas was blown in in the presence of 0.20 g of 5% palladium-carbon, as a catalyst, at room temperature for 3 hours under one atmospheric pressure while stirring. The reaction liquid was filtered under suction to remove the catalyst therefrom, and the solvent was removed by distillation to obtain 0.24 g (yield: 95%) of 3,4-dihydro-2,2-dimethyl-3-hydroxy-4-(1-piperidinyl)-6,7-diamino-2H-benzo[b]pyran as a dark red oil. 0.12 g (0.86 mmol) of thionylaniline and 4 g of benzenewere added thereto and heated under reflux for 2.5 hours. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate-ethanol=1:3) to obtain 60 mg (yield: 23%) of the intended compound as an yellow solid.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered under suction
  3. customto remove the catalyst
  4. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-464604482d42484dbe73dd31bd46bcc9
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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