Phosphorus oxychloride → 12-Chlorobenz[b]acridine

HRID 1608484Notes

Reaction equation

HRID 1608484 reaction equation
[NH:1]([C:8]1[C:9]([C:18](O)=O)=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:18]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:8]2[C:9]=1[CH:10]=[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]1=[CH:17]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1388882-Naphthalenecarboxylic acid, 3-(phenylamino)-

Product 1

HCID 1476981312-Chlorobenz[b]acridineYield 95%

Conditions

Temperature
150 °C

Procedure

A mixture of 3-anilino-2-naphthoic acid (10.0 g, 37.98 mmol) and phosphorous oxychloride (35.4 ml, 379.8 mmol) was refluxed at 150° C. under nitrogen with stirring for 2 hours. The resulting purple mixture was cooled and evaporated under reduced pressure to dryness. The content was added with stirring to a mixture of chloroform/ice/conc. ammonium hydroxide (200 ml/200 g/200 ml). The chloroform layer was separated and dried over calcium chloride. Removal of the solvent under reduced pressure gave 12-chlorobenz[b]acridine (9.4 g, 95%). Rf 0.8 (silica gel, hexane/ethyl acetate 2:1). MS (EI): m/z 263 (M).

Workup

  1. temperatureThe resulting purple mixture was cooled
  2. customevaporated under reduced pressure to dryness
  3. additionThe content was added
  4. stirringwith stirring to a mixture of chloroform/ice/conc
  5. customThe chloroform layer was separated
  6. dry with materialdried over calcium chloride
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-68d856f50c5943f4b3815fe78a3fd4ba
Source dataset
uspto-grants-1995_03
Patent number
US05395752

Reaction notes

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