Hydrochloric Acid → Hydrochloric Acid

HRID 521016Notes

Reaction equation

HRID 521016 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-])=O.[ClH:17]>[Pd].O=[Pt]=O.CO>[NH:9]1[CH2:10][CH2:11][CH2:12][C@@H:13]2[C:14]3[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][C:6]=3[CH2:7][C@H:8]12.[ClH:17]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 126342947-nitro-9H-indeno[2,1-b]pyridine

Product 2

HCID 313Hydrochloric AcidHCID 58294569cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-7-ylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitro-9H-indeno[2,1-b]pyridine (3.25 g), 10% palladium on carbon (0.35 g), and methanol (50 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 22 h. PtO2 (0.50 g) and 4 M aqueous hydrochloric acid (3.2 mL) are then added and shaking is continued under hydrogen atmosphere (1 bar) at room temperature for another 22 h. The catalysts are separated by filtration and the filtrate is concentrated to give the crude title compound as its hydrochloric acid salt that is used without further purification or transformed to the free base by treatment with aqueous NaOH solution and extraction into ethyl acetate. Yield: 4.20 g (ca. 80% pure); LC (method 1): tR=0.52 min; Mass spectrum (ESI+): m/z=189 [M+H]+.

Workup

  1. stirringshaking
  2. customat room temperature
  3. customfor another 22 h
  4. customThe catalysts are separated by filtration
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-3ea8d5ca11ed41b296736aab7e4919c6
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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