2-Cyano-5-nitroindane → 5-Amino-2-cyanoindane

HRID 1708559Notes

Reaction equation

HRID 1708559 reaction equation
[C:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:12]([O-])=O)[CH:9]=2)[CH2:4]1)#[N:2]>CO.ClCCl.[Pd]>[NH2:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][CH:3]([C:1]#[N:2])[CH2:11]2

Participants

4

Reactant 1

HCID 189589622-Cyano-5-nitroindane

Product 1

HCID 189589645-Amino-2-cyanoindaneYield 103.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 2-cyano-5-nitroindane (11.90 g, 63.3 mmol) in methanol/dichloromethane=1:1 (200 ml) was hydrogenated over 10% palladium on charcoal (1.2 g) at 30 p.s.i and 20° C. for 5 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give 5-amino-2-cyanoindane (10.4 g) which was used directly for the next reaction. A portion, recrystallised from ethanol, formed pinkish needles, m.p. 73°-76° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-59ebf44a699a4b7a8da098522783093f
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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