Phosphorus oxychloride → 4-Chlorothieno[2,3-c]quinoline-7-carbonitrile

HRID 1919674Notes

Reaction equation

HRID 1919674 reaction equation
O=[C:2]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=2[NH:3]1.P(Cl)(Cl)([Cl:19])=O>C(#N)C>[Cl:19][C:2]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]#[N:16])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 575006864-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile

Product 1

HCID 575006874-Chlorothieno[2,3-c]quinoline-7-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile (1.0 eq, 1.22 g, 5.40 mmol) was stirred under reflux in acetonitrile (12 ml) and phosphorus oxychloride (5.0 eq, 2.5 ml, 26.8 mmol) for 6 hours. The volatiles were removed in vacuo, water and ice were added. The resulting solid was filtered, washed with water and dried to afford 4-chlorothieno[2,3-c]quinoline-7-carbonitrile as a light brown solid (1.18 g, 90% yield). LCMS (ES)>95% pure, m/z 245 [M+1]+.

Workup

  1. customThe volatiles were removed in vacuo, water and ice
  2. additionwere added
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ddb916da91024feba5003e607105486b
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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