Hydrochloric Acid → HCID 21551717, compound

HRID 268215Notes

Reaction equation

HRID 268215 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=O.[CH3:12][CH:13]1[CH2:18][C:17](=[O:19])[CH2:16][C:15](=O)[CH2:14]1.[ClH:21].O>O1CCCC1>[Cl:21][C:9]1[CH:8]=[C:5]2[C:4]([N:1]([OH:3])[C:15]3[CH2:14][CH:13]([CH3:12])[CH2:18][C:17](=[O:19])[C:16]=3[C:6]2=[O:7])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 111012-NitrobenzaldehydeHCID 4580955-Methylcyclohexane-1,3-dione

Product 1

HCID 21551717HCID 21551717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30.2 g (0.2 mole) of 2-nitrobezaldehyde and 25.2 g (0.2 mole) of 5-methyl-1,3-cyclohexane-dione were dissolved in 300 ml of tetrahydrofurane, the solution was saturated at 18° C with hydrogen chloride and allowed to stand for 4 days at room temperature. Water was added, the oily layer was separated and stirred with methanol. The crystals that had formed were filtered off, washed with methanol and dissolved and recrystallized from glacial acetic acid. 9.5 g (17 % of the theory) of 7-chloro-3-methyl-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9(10H)-acridone having a decomposition point of 255° C were obtained.

Workup

  1. customthe oily layer was separated
  2. customThe crystals that had formed
  3. filtrationwere filtered off
  4. washwashed with methanol
  5. dissolutiondissolved
  6. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-b7b28e330e6243c899d66b4fb4eab0ff
Source dataset
uspto-grants-1976_03
Patent number
US03947449

Reaction notes

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