Phosphorus oxychloride → 4-Chloro-7-methylquinoline-2-carbonitrile

HRID 2422535Notes

Reaction equation

HRID 2422535 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[N+:9]([O-])[C:8]([C:13]#[N:14])=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:13]#[N:14])[CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 667907327-Methylquinoline-2-carbonitrile 1-oxide

Product 1

HCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

Conditions

Temperature
100 °C

Procedure

A mixture of 7-methylquinoline-2-carbonitrile 1-oxide (11.5 g, 63 mmol) and phosphorus oxychloride (47 mL, 500 mmol) was heated at 100° C. for 10 min then at 200° C. for 20 min. The reaction mixture was poured into crushed ice and the precipitate was filtered. The crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane) to provide the title compound. 1HNMR (400 MHz, acetone-d6): δ 8.25 (d, 1H), 8.10 (s, 1H), 8.00 (d, 1H), 7.82 (dd, 1H), 2.65 (s, 3H).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. filtrationthe precipitate was filtered
  4. customThe crude material was then purified by flash chromatography on silica gel (eluting solvent: 3% acetone in dichloromethane)

Sources & evidence

ORD record
ord-214f58c58b894c908e413bc793447d6b
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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