Diethyl Ether → 8-Methoxy-1,2,3,4-tetrahydro-9-acridinamine

HRID 981919Notes

Reaction equation

HRID 981919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:11])[C:8]=1[C:9]#[N:10].CCO[CH2:15][CH3:16]>[N+](C1C=CC=CC=1)([O-])=O.C1(=O)CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:8]=1[C:9]([NH2:10])=[C:15]1[C:16]([CH2:4][CH2:3][CH2:8][CH2:7]1)=[N:11]2

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 127157142-Amino-6-methoxybenzonitrile

Product 1

HCID 197702928-Methoxy-1,2,3,4-tetrahydro-9-acridinamine

Reagents, catalysts & solvents 2

HCID 7416NitrobenzeneSolventHCID 7967CyclohexanoneSolvent

Conditions

Temperature
125 °C

Procedure

6-Methoxyanthranilonitrile (14.0 g) was dissolved in nitrobenzene (150 ml) and cyclohexanone (18.45 g), and freshly fused zinc chloride (25.6 g) was added. The reaction mixture was warmed at 125° C. for 1.5 hr, cooled to room temperature, and poured into ether (1 l). The solid was collected, washed with ether, and distributed between 2-butanone and ammonium hydroxide. The organic phase was washed with brine, dried, filtered, and evaporated. The residue was recrystallized two times from ethyl acetate to give 13.7 g (63.8%), mp 187°-188° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe solid was collected
  3. washwashed with ether
  4. washThe organic phase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized two times from ethyl acetate
  9. customto give 13.7 g (63.8%), mp 187°-188° C.

Sources & evidence

ORD record
ord-743d82cf4e014a36a800348797365806
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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