HCID 59408994, compound → HCID 16743122, compound

HRID 1894724Notes

Reaction equation

HRID 1894724 reaction equation
[C:1]1(/[CH:13]=[CH:14]/[C:15]#[N:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[H][H]>CO.[Pd]>[C:1]1([CH2:13][CH2:14][C:15]#[N:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

5

Reactant 2

HCID 59408994HCID 59408994, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16743122HCID 16743122, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-acrylonitrile (348 mg, 1.7 mmol) and 10% Pd—C (50 mg) in methanol (20 ml) were stirred at room temperature under 1 atmosphere of hydrogen gas for 6 hours. The mixture was filtered through celite washed with methanol and evaporated to dryness to yield 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-propionitrile as an off white solid (310 mg). 400 MHz 1H NMR (CDCl3) δ: 7.32 (d, J=8.4 Hz, 1H), 7.03-6.96 (m, 2H), 6.91 (d, J=6.8 Hz, 1H), 4.11 (t, J=5.6 Hz, 2H), 3.11 (t, J=6.8 Hz, 2H), 2.97 (t, J=6.4 Hz, 2H), 2.66 (t, J=7.2 Hz, 2H), 2.26-2.19 (m, 2H); LCMS: 211 [M+H].

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with methanol
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-912c869ac0bb4c14b43e8a421773a513
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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