Triethylamine → (6-Amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetonitrile

HRID 340683Notes

Reaction equation

HRID 340683 reaction equation
Br[C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([O:14][CH3:15])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[CH:16][C:17]#[N:18].C(N(CC)CC)C>C(OCC)(=O)C.[C].[Pd]>[NH2:11][C:9]1[C:8]([O:14][CH3:15])=[C:7]2[C:3]([CH2:4][CH2:5][C:6]2=[CH:16][C:17]#[N:18])=[CH:2][CH:10]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 67355123(4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile

Product 1

HCID 67353001(6-Amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)acetonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile (47.0 mg, 0.152 mmol) and triethylamine (22.3 μL, 0.160 mmol) were dissolved in ethyl acetate (1.5 mL), a 10% palladium-carbon powder (10 mg) was added, and the mixture was stirred at room temperature for 1.5 hr under a hydrogen atmosphere. The catalyst was filtered off using celite, and the filtrate was concentrated under reduced pressure to give the title compound (30.4 mg, yield 100%).

Workup

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

Sources & evidence

ORD record
ord-3ecdb2e263e941cead221f4a37cd56f4
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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