Acetone → HCID 57781096, compound

HRID 1690759Notes

Reaction equation

HRID 1690759 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.ClCCl.[CH3:8][C:9]([CH3:11])=O.[C:12]1(=[O:23])[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]2[CH2:13]1>C(Cl)(Cl)Cl>[CH:1]1([N:4]2[C:9]([CH3:11])([CH3:8])[CH:13]([C:12]([OH:18])=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:17])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 12801Homophthalic anhydrideHCID 69828Cyclopropylamine

Product 1

HCID 57781096HCID 57781096, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To type-I neutral alumina (16 g) is added cyclopropylamine (4.2 mL, 60 mmol) followed by dichloromethane (10 mL). The resulting slurry is cooled to 0° C. and acetone (6 mL, 82 mmol) is added slowly. The slurry is brought to room temperature and permitted to stir for 9 h, at which time the reaction mixture is filtered through a fritted funnel. The alumina cake is washed with chloroform (150 mL) and homophthalic anhydride (10.0 g, 62 mmol) is added to the combined filtrate. The resulting yellow solution is permitted to stir for 15 h at which time it is concentrated in vacuo and the resulting residue is dissolved in glacial acetic acid (130 mL) and placed at reflux for 4 h. The reaction mixture is then cooled to room temperature and concentrated to dryness in vacuo. The reaction mixture is then purified by silica gel flash chromatography [(6% ethyl acetate/0.08% acetic acid/93.92% dichloromethane) to (18% ethyl acetate/0.24% acetic acid/81.76% dichloromethane)] to afford 2-cyclopropyl-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid as an off-white powder; MS (ESI) m/z 260.1 (M+H).

Workup

  1. customis brought to room temperature
  2. filtrationis filtered through a fritted funnel
  3. additionis added to the combined filtrate
  4. stirringto stir for 15 h at which time it
  5. concentrationis concentrated in vacuo
  6. dissolutionthe resulting residue is dissolved in glacial acetic acid (130 mL)
  7. temperatureat reflux for 4 h
  8. temperatureThe reaction mixture is then cooled to room temperature
  9. concentrationconcentrated to dryness in vacuo
  10. customThe reaction mixture is then purified by silica gel flash chromatography [(6% ethyl acetate/0.08% acetic acid/93.92% dichloromethane) to (18% ethyl acetate/0.24% acetic acid/81.76% dichloromethane)]

Sources & evidence

ORD record
ord-7b6eb49b7bc04362893a5cf7e4b30c87
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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