HCID 14673956, compound → HCID 14674145, compound

HRID 2286198Notes

Reaction equation

HRID 2286198 reaction equation
[NH2:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][C:5]2[O:6][C:7]([CH3:18])([CH3:17])[C@@H:8]([OH:16])[C@H:9]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:4]=2[CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:20]([NH2:21])=[CH:19][C:5]2[O:6][C:7]([CH3:17])([CH3:18])[C@@H:8]([OH:16])[C@H:9]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14673956HCID 14673956, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14674145HCID 14674145, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-amino-3,4-dihydro-2,2-dimethyl-7-nitro-trans-4-piperidino-2H-benzo[b]pyran-3-ol (140 mg) in ethanol (30 ml) was hydrogenated over 5% palladium-charcoal (0.1 g) until uptake of hydrogen ceased. The solution was filtered (Kieselguhr) and evaporated to dryness in vacuo to give unstable 6,7-diamino-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2H-benzo[b]pyran-3-ol (0.12 g) which was used immediately in the following reactions. Rf (0.3) in ethyl acetate-hexane 1:2 (colourless spot) compared with starting material with Rf (0.6) as an orange spot.

Workup

  1. filtrationThe solution was filtered (Kieselguhr)
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d4ce725892fa4cb68d88490d20122cb9
Source dataset
uspto-grants-1982_04
Patent number
US04327099

Reaction notes

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