Oxalyl chloride → 2-(Acetylamino)methyl-5-(3-methoxycarbonylpropionyl)indane

HRID 2293101Notes

Reaction equation

HRID 2293101 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:14][CH3:15])(=[O:13])[CH2:8][CH2:9][C:10]([O-:12])=O.[C:16]([NH:19][CH2:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.ClC(Cl)C>[C:16]([NH:19][CH2:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:10](=[O:12])[CH2:9][CH2:8][C:7]([O:14][CH3:15])=[O:13])[CH:27]=2)[CH2:22]1)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 6930703Mono-Methyl SuccinateHCID 214762872-(Acetylaminomethyl)indane

Product 1

HCID 214763072-(Acetylamino)methyl-5-(3-methoxycarbonylpropionyl)indaneYield 93.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

46.4 g of oxalyl chloride and 2 drops of dimethyl-formamide were added to 48.3 g of monomethyl succinate dissolved in 840 ml of dichloroethane. The mixture was stirred at room temperature for 5 hours. Then, under ice cooling, 34.6 g of 2-(acetylaminomethyl)indane dissolved in 280 ml of dichloroethane and 97.6 g of anhydrous aluminum chloride were added to the reaction mixture. After the mixture was stirred for 1 hour, the reaction mixture was poured into ice water. After the organic layer was collected by separation, washed with water and dried, the solvent was removed to obtain 51.8 g of 2-(acetylaminomethyl)-5-(3-methoxycarbonylpropionyl)indane. m.p.: 139° to 140° C.

Workup

  1. stirringAfter the mixture was stirred for 1 hour
  2. customAfter the organic layer was collected by separation
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-9b1b1f762b41442cbb2ff312c4701767
Source dataset
uspto-grants-1997_11
Patent number
US05686452

Reaction notes

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