Acetic Acid → 4-nitro-2,3-dihydro-1H-indene-2-carboxylic acid

HRID 1266145Notes

Reaction equation

HRID 1266145 reaction equation
C([C:3]1([C:15]([O:17]CC)=[O:16])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:12]([O-:14])=[O:13])[CH2:4]1)#N.C(O)(=O)C.Cl>O>[N+:12]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH:3]([C:15]([OH:17])=[O:16])[CH2:4]2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 185489912-Cyano-2-ethoxycarbonyl-4-nitroindan

Product 1

HCID 185458324-nitro-2,3-dihydro-1H-indene-2-carboxylic acidYield 107.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-cyano-2-ethoxycarbonyl-4-nitroindan (21 g, 81 mmol), acetic acid (290 mL), hydrochloric acid (37%, 130 mL) and water (140 mL) was stirred under reflux temperature over night. The acid was evaporated in vacuo and the residue was made alkaline with a 2 M sodium hydroxide solution. The mixture was stirred at room temperature, insoluble matter was filtered and the filtrate was acidified with hydrochloric acid. The obtained precipitate was filtered and washed with water to afford 18 gram of the crude acid: mp ˜140° C.; EIMS (70 eV) m/z (relative intensity) 207 (40, M+).

Workup

  1. temperatureunder reflux temperature over night
  2. customThe acid was evaporated in vacuo
  3. stirringThe mixture was stirred at room temperature
  4. filtrationinsoluble matter was filtered
  5. filtrationThe obtained precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-469d7ed0a29e4029aa28ffc9e8bd480e
Source dataset
uspto-grants-2003_04
Patent number
US06548498B1

Reaction notes

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