Cyanoacetic acid → HCID 59408992, compound

HRID 1894722Notes

Reaction equation

HRID 1894722 reaction equation
[CH:1]1[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.[C:13]([CH2:15][C:16](O)=[O:17])#[N:14]>C(OC(=O)C)(=O)C>[C:1]1([C:16](=[O:17])[CH2:15][C:13]#[N:14])[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

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 156456291-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene

Product 1

HCID 59408992HCID 59408992, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (3.0 g, 19.1 mmol) and cyanoacetic acid (1.7 g, 20.0 mmol) in acetic anhydride (50 ml) were heated to 90° C. for 1.5 hours. After cooling to room temperature the product precipitated out, was filtered off, washed with cold methanol and dried under reduced pressure to obtain 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxo-propionitrile as cream colored crystals (3.457 g). 400 MHz 1H NMR (CDCl3) δ: 7.99 (d, J=7.6 Hz 1H), 7.83 (s, 1H), 7.25 (s, 1H), 7.07 (d, J=6.4 Hz, 1H), 4.23 (m, 2H), 3.88 (s, 2H), 3.01 (m, 2H), 2.28 (m, 2H); LCMS: 225 [M+H]

Workup

  1. customprecipitated out
  2. filtrationwas filtered off
  3. washwashed with cold methanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f3cff7b1b1a4473e82c076a898821ff5
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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