HCID 14673954, compound → HCID 14674144, compound

HRID 581029Notes

Reaction equation

HRID 581029 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]>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

4

Reactant 1

HCID 14673954HCID 14673954, compound

Product 1

HCID 14674144HCID 14674144, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.14 g (0.44 mmol) of 3,4-dihydro-2,2-dimethyl-3-hydroxy-4-(1-piperidinyl)-6-amino-7-nitro-2H-benzo[b]pyran were dissolved in 23.7 g of ethanol and hydroge gas was blown in the presence of 0.10 g of 5% palladiumcarbon, as a catalyst, for 3 hours at room temperature 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 0.12 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. As being unstable, this oil was directly used in the next diazotization.

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-71c68c36015040518a8cbd50045e7c50
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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