2-Tetralone → HCID 89657730, compound

HRID 521414Notes

Reaction equation

HRID 521414 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7]CC)=[O:6])[C:3]=1[C:13]([O:15]CC)=O.NC1C=CC=C(C(OC)=O)C=1C(OC)=O.[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][C:34]1=O.[Cl-].[Cl-].[Cl-].[Al+3]>CO>[O:15]=[C:13]1[C:38]2[C:37]3[CH:36]=[CH:35][CH:34]=[CH:33][C:42]=3[CH2:41][CH2:40][C:39]=2[NH:1][C:2]2[C:3]1=[C:4]([C:5]([OH:7])=[O:6])[CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 4

HCID 682662-TetraloneHCID 6451240Aluminum(III) ChlorideHCID 11207123Diethyl 3-aminobenzene-1,2-dicarboxylateHCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylate

Product 1

HCID 89657730HCID 89657730, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of diethyl 3-aminophthalate and dimethyl 3-aminophthalate (1.0 g, 3.82 mmol), 3,4-dihydronaphthalen-2(1H)-one (0.61 g, 4.2 mmol), and aluminum trichloride (0.51 g, 3.82 mmol) was placed in a sealed tube and heated to 80° C. for 1 hour and then 130° C. for additional 4 hours. The mixture was cooled to room temperature, treated with methanol and concentrated. The remaining residue was chromatographed on silica gel using eluant of 3.2% methanol in dichloromethane and then purified by recrystalization in ethyl acetate and methanol to give the product (0.36 g, 30%) as a light brown solid. MS (ESI) m/e [M+1]+292.

Workup

  1. customwas placed in a sealed tube
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customThe remaining residue was chromatographed on silica gel using eluant of 3.2% methanol in dichloromethane
  5. custompurified by recrystalization in ethyl acetate

Sources & evidence

ORD record
ord-55857f90e4574db1a74a7a6a0858d98b
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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