Hydrochloric Acid → 7-Chloro-10-[(4-dimethylaminobutyl)amino]-2-methoxypyrido[3,2-b]quinoline dihydrochloride

HRID 903143Notes

Reaction equation

HRID 903143 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](Cl)=[C:7]3[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:8]3=[N:9][C:10]=2[CH:11]=1.[CH3:19][N:20]([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH3:21].C1(O)C=CC=CC=1.[ClH:34]>CC(C)=O.C(O)C>[ClH:1].[ClH:34].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([NH:26][CH2:25][CH2:24][CH2:23][CH2:22][N:20]([CH3:21])[CH3:19])=[C:7]3[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:8]3=[N:9][C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 231071-Aza-6,9-dichloro-2-methoxyacridineHCID 770634-Dimethylaminobutylamine

Product 1

HCID 233378097-Chloro-10-[(4-dimethylaminobutyl)amino]-2-methoxypyrido[3,2-b]quinoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4.2 g. of 7,10-dichloro-2-methoxypyrido [3,2-b]quinoline, 1.6 g. of dimethylaminobutylamine and 10 g. of phenol is stirred and heated on a steam bath for 3 hours. The reaction is cooled, 30 ml. of ethanol is added and this mixture is poured into a mixture of 300 ml. of acetone and 3.75 ml. of concentrated hydrochloric acid. The yellow precipitate is collected, washed with acetone, air-dried and recrystallized from 100 ml. of 95% alcohol giving the desired product as yellow crystals, mp. 237°-238° C. (dec.)

Workup

  1. additionA mixture of 4.2 g
  2. temperatureheated on a steam bath for 3 hours
  3. temperatureThe reaction is cooled
  4. additionthis mixture is poured into a mixture of 300 ml
  5. customThe yellow precipitate is collected
  6. washwashed with acetone
  7. customair-dried
  8. customrecrystallized from 100 ml

Sources & evidence

ORD record
ord-08a98d10d55740a6baee2dbe2b59e400
Source dataset
uspto-grants-1980_10
Patent number
US04226869

Reaction notes

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