3-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde → HCID 68705972, compound

HRID 14473Notes

Reaction equation

HRID 14473 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:28])[C:10]3[CH:11]=[CH:12][C:13]4[N:25](C=O)[CH2:24][CH2:23][CH2:22][O:21][C:14]=4[C:15]=3[O:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[CH:4][CH:3]=1>Cl.CO.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:28])[C:10]3[CH:11]=[CH:12][C:13]4[NH:25][CH2:24][CH2:23][CH2:22][O:21][C:14]=4[C:15]=3[O:16][C:17]=2[CH:18]([CH3:20])[CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 866256113-(4-Chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde

Product 1

HCID 68705972HCID 68705972, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 3-(4-chlorophenyl)-2-isopropyl-4-oxo-9,10-dihydro-4H,8H-1,11-dioxa-7-aza-cyclohepta[a]naphthalene-7-carbaldehyde (0.063 g, 0.158 mmol) in 1M HCl solution (4 ml) and methanol (6 ml) is heated under reflux for 1 h under a nitrogen atmosphere. The mixture is allowed to cool to room temperature, and the methanol solvent is removed by evaporation in vacuo. The concentrated mixture is diluted with water (5 ml) and treated with solid sodium hydrogen carbonate, until a pH of 7-8 is attained. The mixture is washed successively with ethyl acetate and methylene chloride. The combined organic phases are dried (magnesium sulfate) and filtered, and the solvent is removed by evaporation in vacuo to afford a crude orange solid. This is stirred overnight in a solution of 2M HCl in diethyl ether (3 ml), filtered and dried at room temperature under high vacuum to give the title compound as a cream-coloured solid.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 h under a nitrogen atmosphere
  3. customthe methanol solvent is removed by evaporation in vacuo
  4. additionThe concentrated mixture is diluted with water (5 ml)
  5. additiontreated with solid sodium hydrogen carbonate, until a pH of 7-8
  6. washThe mixture is washed successively with ethyl acetate and methylene chloride
  7. dry with materialThe combined organic phases are dried (magnesium sulfate)
  8. filtrationfiltered
  9. customthe solvent is removed by evaporation in vacuo
  10. customto afford a crude orange solid
  11. filtrationfiltered
  12. customdried at room temperature under high vacuum

Sources & evidence

ORD record
ord-664239bad5354b919da3e6d5ae5d116f
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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