Hydrochloric Acid → HCID 13268057, compound

HRID 1980841Notes

Reaction equation

HRID 1980841 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][CH2:18]2.CO[Na].Cl>C1C=CC=CC=1>[CH2:18]1[C:19]2[C:15](=[C:14]([NH:13][C:4](=[O:6])[C:3]3[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=3[CH3:1])[CH:22]=[CH:21][CH:20]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66598Ethyl 2-methylbenzoateHCID 1225694-AminoindanHCID 178418582HCID 178418582, compound

Product 1

HCID 13268057HCID 13268057, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.0 g of ethyl o-methylbenzoate (12.2 m mol), 1.62 g of 4-aminoindan (12.2 m mol), 0.72 g of CH3ONa and 30 ml of benzene is stirred for 10 hours under reflux. After ice-cooling, the mixture is added to dilute hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with water and concentrated. The resulting crystals are washed with n-hexane to give 2.0 g of N-4-indanyl-o-methylbenzamide (yield: 65.4%).

Workup

  1. temperatureunder reflux
  2. temperatureAfter ice-cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. concentrationconcentrated
  6. washThe resulting crystals are washed with n-hexane

Sources & evidence

ORD record
ord-48fd81615a8b46999622418c18902656
Source dataset
uspto-grants-1985_04
Patent number
US04511581

Reaction notes

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