Phosphorus oxychloride → HCID 5156493, compound

HRID 968490Notes

Reaction equation

HRID 968490 reaction equation
[N+:1]([C:4]1[C:5](=O)[NH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].C(#N)C>[Cl:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3323695HCID 3323695, compound

Product 1

HCID 5156493HCID 5156493, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of intermediate (8) (0.072 mol) and BTEAC (0.0362 mol) in ACN (150 ml) was stirred at room temperature. Phosphoric trichloride (0.222 mol) was added dropwise. The mixture was stirred and refluxed for 8 hours. The solvent was evaporated till dryness. The residue was poured out into water and NH4OH. The mixture was extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 15 g of 2-chloro-5,6,7,8-tetrahydro-3-nitroquinoline (intermediate 9).

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe solvent was evaporated till dryness
  3. additionThe residue was poured out into water and NH4OH
  4. extractionThe mixture was extracted with DCM
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-63c517d4ac0a4d029f4ce84c232c7aa7
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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