Hydrochloric Acid → 9-Amino-1,2,3,4-tetrahydroacridine hydrate

HRID 6221

Reaction equation

HRID 6221 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.Cl>>[OH2:16].[NH2:5][C:4]1[C:3]2[C:2]([N:1]=[C:10]3[C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 7967CyclohexanoneHCID 729132-Aminobenzonitrile

Product 1

HCID 197952369-Amino-1,2,3,4-tetrahydroacridine hydrateYield 67%

Procedure

A mixture of 2-aminobenzonitrile (120 g), cyclohexanone (115.8 ml), conc hydrochloric acid (9.2 ml), and cuprous chloride (1.21 g) was heated under reflux for 3 days, with stirring. At the end of each 24 hr period, additional cuprous chloride (1.21 g) was added. At the end of the 3rd day, additional conc hydrochloric acid (47.3 ml) was added, and the mixture was cooled to ambient temperature. The precipitate was collected and washed with 10% hydrochloric acid to provide 160 g (67.0%) of 9-amino-1,2,3,4-tetrahydroacridine hydrate, mp 180°-185°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. customThe precipitate was collected
  4. washwashed with 10% hydrochloric acid

Sources & evidence

ORD record
ord-ef26d013c4cc405e8068592ad63dfa26
Source dataset
uspto-grants-1993_09
Patent number
US05247091

Linked notes

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