Phosphorus oxychloride → Hydrochloric Acid

HRID 1970993Notes

Reaction equation

HRID 1970993 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14](=O)[NH:13][CH:12]=[C:11]([C:16]#[N:17])[C:7]=3[NH:8][C:9]=2[CH:10]=1.O=P(Cl)(Cl)[Cl:20]>O1CCOCC1>[Cl:20][C:14]1[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[NH:8][C:7]=2[C:11]([C:16]#[N:17])=[CH:12][N:13]=1.[ClH:1]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 565951917-chloro-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-4-carbonitrile

Product 2

HCID 313Hydrochloric AcidHCID 565950571,7-dichloro-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
93 °C

Procedure

To a slurry of 7-chloro-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-4-carbonitrile (24.95 g, 102 mmol) in dioxane (200 mL) was added POCl3 (79 g, 512 mmol) dropwise at 93° C. The reaction mixture was left to stir at 93° C. for 5 h, cooled to room temperature, and left to stir overnight. The reaction mixture was filtered, washed with MTBE, and dried to give the title compound as an HCl salt. 1H NMR (600 MHz, CD3SOCD3) δ 13.33 (s, 1H); 8.80 (s, 1H); 8.39 (d, 1H); 7.70 (d, 1H); 7.50 (dd, 1H). LRMS (APCI) calc'd for (C12H5Cl2N3) [M+H]+, 262.0. found 261.9.

Workup

  1. waitThe reaction mixture was left
  2. temperaturecooled to room temperature
  3. waitleft
  4. stirringto stir overnight
  5. filtrationThe reaction mixture was filtered
  6. washwashed with MTBE
  7. customdried

Sources & evidence

ORD record
ord-db93b9f5d6fb41339b92e8d508a93500
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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