Hydrochloric Acid → HCID 66741339, compound

HRID 587873Notes

Reaction equation

HRID 587873 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=2)[C:4]1=[O:14].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(NC(C)C)(C)C.Cl>ClCCl>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:10]([CH2:11][CH:3]([NH:2][C:16](=[O:17])[O:18][CH2:19][CH3:20])[C:4]2=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 10928Ethyl chloroformateHCID 241816742-Amino-6-methoxy-1-indanone hydrochloride

Product 1

HCID 66741339HCID 66741339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 2-amino-6-methoxy-2,3-dihydro-1H-inden-1-one hydrochloride (15.4 g, 72.1 mmol) in dichloromethane was added ethyl chloroformate (10.38 ml, 108 mmol) followed by dropwise addition of a solution of diisopropylamine (25.2 ml, 144 mmol) in 10 ml dichloromethane. The reaction mixture was stirred at room temperature over night. Added 1N hydrochloric acid, diluted with dichloromethane, separated organic layer and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed subsequently with water, sodium bicarbonate and brine, dried, filtered and evaporated to obtain the product (ethyl 6-methoxy-1-oxo-2,3-dihydro-1H-inden-2-ylcarbamate) as a purple solid. m=16.4 g (95%)

Workup

  1. customseparated organic layer
  2. extractionthe aqueous layer was extracted twice with dichloromethane
  3. washThe combined organic layers were washed subsequently with water, sodium bicarbonate and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-055d95c3b2bd4654974b16c4e86073c5
Source dataset
uspto-grants-2016_01
Patent number
US09227930B2

Reaction notes

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