Dichloromethane → HCID 10613124, compound

HRID 1457935Notes

Reaction equation

HRID 1457935 reaction equation
C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:8][C:9]1[O:10][C:11](=[O:29])[CH:12]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[CH:18]=[CH:17][C:16]=2[O:27][CH3:28])[N:13]=1>C(OC(=O)C)(=O)C>[O:29]=[C:11]1[C:23]2=[C:24]3[C:19](=[CH:20][CH:21]=[C:22]2[O:25][CH3:26])[CH:18]=[CH:17][C:16]([O:27][CH3:28])=[C:15]3[CH2:14][CH:12]1[NH:13][C:9](=[O:10])[CH3:8].[O:29]=[C:11]1[C:23]2=[C:24]3[C:19](=[CH:20][CH:21]=[C:22]2[OH:25])[CH:18]=[CH:17][C:16]([O:27][CH3:28])=[C:15]3[CH2:14][CH:12]1[NH:13][C:9](=[O:10])[CH3:8]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 10494365HCID 10494365, compound

Product 2

HCID 10613124HCID 10613124, compoundHCID 10709268HCID 10709268, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

The compound obtained in Preparation 33 (5 mmol; 1.65 g) is dissolved in 10 cm3 of acetic anhydride and the reaction medium is maintained at the reflux temperature of the solvent for 40 min. The excess anhydride is evaporated to dryness with a trolley pump in order to isolate the 2-methyl-4-[(2,7-dimethoxynaphth-1-yl)methyl]oxazolin-5-one, which is used without further purification. 30 cm3 of anhydrous CH2Cl2 and aluminum chloride (18 mmol; 2.37 g) are introduced into a three-necked flask placed under an inert atmosphere, followed by dropwise addition of 2-methyl-4-[(2,7-dimethoxynaphth-1-yl)methyl]oxazolin-5-one (6 mmol; 1.78 g) dissolved in 40 cm3 of the same solvent. The reaction medium is maintained at 60° C. for 2 h and, after cooling, is then poured onto an ice/concentrated HCl mixture and stirred for 1 h. The organic phase is recovered and the aqueous phase is extracted several times with CH2Cl2. The combined organic phases are dried over MgSO4 and then evaporated. The residue is purified by chromatography on a column of silica gel (particle size 60-200 μm); eluent: CH2Cl2 then CH2Cl2 :MeOH 99:1 v/v. N-(1-oxo-4,9-dimethoxy-2,3-dihydro-1H-phenalen-2-yl)acetamide (a) and N-(1-oxo-9-hydroxy-4-methoxy-2,3-dihydro-1H-phenalen-2-yl)acetamide (β) are obtained.

Workup

  1. customThe compound obtained in Preparation 33 (5 mmol; 1.65 g)
  2. temperaturethe reaction medium is maintained at the reflux temperature of the solvent for 40 min
  3. customThe excess anhydride is evaporated to dryness with a trolley pump in order
  4. customto isolate the 2-methyl-4-[(2,7-dimethoxynaphth-1-yl)methyl]oxazolin-5-one, which
  5. customis used without further purification
  6. temperatureafter cooling
  7. customThe organic phase is recovered
  8. extractionthe aqueous phase is extracted several times with CH2Cl2
  9. dry with materialThe combined organic phases are dried over MgSO4
  10. customevaporated
  11. customThe residue is purified by chromatography on a column of silica gel (particle size 60-200 μm)

Sources & evidence

ORD record
ord-eb56b64086be41d6b464e4fbb79db989
Source dataset
uspto-grants-1998_12
Patent number
US05849781

Reaction notes

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