HCID 20515398, compound → HCID 67587580, compound

HRID 581030Notes

Reaction equation

HRID 581030 reaction equation
[CH3:1][C:2]1([CH3:22])[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[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:21].[H][H]>C(O)C.[C].[Pd]>[CH3:1][C:2]1([CH3:22])[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[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:21]

Participants

5

Reactant 2

HCID 20515398HCID 20515398, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67587580HCID 67587580, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.20 g (0.65 mmol) of 3,4-dihydro-2,2-dimethyl-3-hydroxy-4-(1-pyrrolidinyl)-6-amino-7-nitro-2H-benzo[b]pyran were dissolved in 34.9 g of ethanol and hydrogen gas was blown in the presence of 0.15 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 distilled off to obtain 170 mg (yield: 94%) of 3,4-dihydro-2,2-dimethyl-3-hydroxy-4-(1-pyrrolidinyl)-6,7-diamino-2H-benzo[b]pyran as a dark red oil.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered under suction
  3. customto remove the catalyst
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ab4a1e0720f04c2396c0b4cdcf4a27e0
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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