Hydrochloric Acid → N,N-Diethyl-4-(9-chloro-9,10-dihydro-10-phenyl-9-acridinyl)aniline

HRID 444297Notes

Reaction equation

HRID 444297 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2(OC)[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:6][CH:5]=1)[CH3:2].[ClH:34]>O1CCCC1>[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([Cl:34])[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13014081HCID 13014081, compound

Product 1

HCID 93461N,N-Diethyl-4-(9-chloro-9,10-dihydro-10-phenyl-9-acridinyl)anilineYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9(p-Diethylaminophenyl)-9-methoxy-10-phenylacridan (12.0 g, 0.0276 mole) is slurried in 150 ml of tetrahydrofuran while anhydrous hydrogen chloride is bubbled in with cooling. The hydrogen chloride is bubbled in until the slurry reaches a pH of 1.0 and a bright yellow color is obtained. The product is collected on a Buchner funnel, washed twice with 10 ml portions of tetrahydrofuran and dried at 50° C. to give 11.6 g (95.8% yield) of 9(p-diethylaminophenyl)-9-chloro-10-phenylacridan.

Workup

  1. customis bubbled in
  2. temperaturewith cooling
  3. customThe hydrogen chloride is bubbled in until the slurry
  4. customa bright yellow color is obtained
  5. customThe product is collected on a Buchner funnel
  6. washwashed twice with 10 ml portions of tetrahydrofuran
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-41c6b5d04df84e44ab94536377e050ce
Source dataset
uspto-grants-1981_04
Patent number
US04263398

Reaction notes

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