Phosphorus oxychloride → 4-Chloro-8-iodoquinoline

HRID 719534Notes

Reaction equation

HRID 719534 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=O.O=P(Cl)(Cl)[Cl:15]>CN(C=O)C>[Cl:15][C:7]1[C:6]2[C:11](=[C:2]([I:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 124036904-Hydroxy-8-iodoquinoline

Product 1

HCID 124036924-Chloro-8-iodoquinolineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Iodo-1H-quinolin-4-one (3.36 g, 8.72 mmol) was suspended in POCl3 (8 mL, 87.2 mmol) and catalytic anhydrous DMF (6.72 μL) was added. The mixture was refluxed for 1 h. The hot crude was poured over ice and the mixture stirred until ice was completely melted. Solid was filtered off, thoroughly washed with water and kept in the vacuum oven overnight to afford 4-chloro-8-iodo-quinoline as a grayish solid (2.47 g, 98%). 1H NMR (DMSO-d6, 400 MHz) δ 7.45 (t, 1H), 7.81 (d, 1H), 8.19 (dd, 1H), 8.45 (dd, 1H), 8.87 (d, 1H). Exact mass calculated for C9H5ClIN 288.92, found 289.9 (MH+).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. additionThe hot crude was poured over ice
  3. filtrationSolid was filtered off
  4. washthoroughly washed with water
  5. customkept in the vacuum oven overnight

Sources & evidence

ORD record
ord-d8e411fc5b2e4a8b894a5ddf1ab02842
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Reaction notes

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