Water → N-(1,1-dimethyl-4-indanyl)-o-methylbenzamide

HRID 1980840Notes

Reaction equation

HRID 1980840 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][C:12]1([CH3:22])[C:20]2[C:15](=[C:16]([NH2:21])[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[CH3:11][C:12]1([CH3:22])[C:20]2[C:15](=[C:16]([NH:21][C:4](=[O:5])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 131156151,1-Dimethyl-2,3-dihydro-1H-inden-4-amine

Product 1

HCID 13268043N-(1,1-dimethyl-4-indanyl)-o-methylbenzamideYield 93.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.81 g of o-methylbenzoyl chloride (5.25 m mol) in 3 ml of tetrahydrofuran is added dropwise to a solution of 0.81 g of 1,1-dimethyl-4-aminoindan (5.00 m mol) and 0.61 g of triethylamine (6.00 m mol) in 10 ml of tetrahydrofuran, while maintaining the reaction mixture at 0° C. by ice-cooling. Then, reaction mixture is stirred over night at room temperature, and water and ethyl acetate are added to the mixture. The organic layer is washed with 5% hydrochloric acid and water and dried over anhydrous sodium sulfate. After the solvent is removed by distillation, the residue is dried to give 1.31 g of N-(1,1-dimethyl-4-indanyl)-o-methylbenzamide (yield: 93.9%).

Workup

  1. temperaturecooling
  2. customThen, reaction mixture
  3. washThe organic layer is washed with 5% hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent is removed by distillation
  6. customthe residue is dried

Sources & evidence

ORD record
ord-f3a9a146354041b1b3b03d921da5ed0a
Source dataset
uspto-grants-1985_04
Patent number
US04511581

Reaction notes

Loading…