Acrylonitrile → 3-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720403Notes

Reaction equation

HRID 720403 reaction equation
[Br-].[F:2][C:3]1[CH:21]=[CH:20][C:6]([C:7](=[O:19])[CH2:8][N+:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:36](#[N:39])[CH:37]=[CH2:38]>CN(C)C=O>[C:36]([C:37]1[CH:38]=[C:8]([C:7](=[O:19])[C:6]2[CH:20]=[CH:21][C:3]([F:2])=[CH:4][CH:5]=2)[N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=12)#[N:39]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 218921811-(4-Fluorophenyl)-2-quinolylethan-1-one, bromide

Product 1

HCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(4-fluoro-phenacyl)-quinolinium bromide (117 mg, 0.338 mmol), tetrapyridinecobalt(II) dichromate (217 mg, 0.356 mmol), sodium bicarbonate (75.7 mg, 0.901 mmol), acrylonitrile (110 μL, 1.67 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 32.6 mg (30%) as a yellow solid. 1H NMR (CDCl3): 8.11 (m, 2H), 8.04 (dd, J=8.52, 0.55 Hz, 1H), 7.86 (dd, J=7.69, 1.65 Hz, 1H), 7.74 (d, J=9.34 Hz, 1H), 7.68 (d, J=9.07 Hz, 1H), 7.62 (ddd, J=8.31, 7.07, 1.72 Hz, 1H), 7.54 (td, J=7.48, 1.19 Hz, 1H), 7.41 (s, 1H), 7.26 (m, 2H).

Workup

  1. customyielded 32.6 mg (30%) as a yellow solid

Sources & evidence

ORD record
ord-95bb726f16db42dfa338c17d1d2b585a
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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