4-Nitrobenzaldehyde → HCID 15728812, compound

HRID 2050500Notes

Reaction equation

HRID 2050500 reaction equation
[CH2:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.N1CCOCC1.[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)([O-:24])=[O:23]>C1(C)C=CC=CC=1>[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[N:15][C:13]2[C:12]3[C:7]([N:6]=[C:5]4[C:14]=2[CH2:1][CH2:2][CH2:3][CH2:4]4)=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 1935TacrineHCID 8083Morpholine

Product 1

HCID 15728812HCID 15728812, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.0 g) was refluxed in 400 ml of toluene containing morpholine (3.5 g) and 4-nitrobenzaldehyde (3.78 g). After forty-eight (48) hours an additional 3.78 g of aldehyde was added and reflux was continued for an additional twenty-four (24) hours. At the end of this time the reaction mixture was concentrated and purified by flash chromatography. Fractions containing the product were concentrated and recrystallized from CH2Cl2 /pentane to give 3.38 g of product, m.p. 237°-238° C.

Workup

  1. temperaturereflux
  2. concentrationAt the end of this time the reaction mixture was concentrated
  3. custompurified by flash chromatography
  4. additionFractions containing the product
  5. concentrationwere concentrated
  6. customrecrystallized from CH2Cl2 /pentane

Sources & evidence

ORD record
ord-d1b68dd8c7b24113ab534c2a17f69c74
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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