Water → Methyl 4-nitro-2,3-dihydro-1H-indene-2-carboxylate

HRID 2110134Notes

Reaction equation

HRID 2110134 reaction equation
[CH3:1][O:2][C:3]([C:5]1(C(OC)=O)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:14]([O-:16])=[O:15])[CH2:6]1)=[O:4].[Cl-].[Li+].O>CS(C)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:14]([O-:16])=[O:15])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 57565181Dimethyl 4-nitro-1H-indene-2,2(3H)-dicarboxylate

Product 1

HCID 53415165Methyl 4-nitro-2,3-dihydro-1H-indene-2-carboxylateYield 67.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of dimethyl-4-nitroindane-2,2-dicarboxylate (4.84 g, 0.0167 mol), lithium chloride (0.84 g, 0.0198 mol), 1.1 mL water, and 18 mL dimethylsulfoxide was heated to 160° C. under nitrogen for two hours. It was then allowed to cool and the dimethylsulfoxide was removed under high vacuum. The residue was purified on silica (10%-100% CH2Cl2 in hexanes) to give 2.5 g white solid (65%).

Workup

  1. temperatureto cool
  2. customthe dimethylsulfoxide was removed under high vacuum
  3. customThe residue was purified on silica (10%-100% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-1956b8a95eb64db99964431bdb57110f
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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