Hydrochloric Acid → 6-(tert-Butyl)indoline

HRID 23477Notes

Reaction equation

HRID 23477 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl>[C:17]([C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH2:9][NH:8]2)=[CH:12][CH:13]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 540929591h-Indole-1-carboxylic acid,6-(1,1-dimethylethyl)-2,3-dihydro-,1,1-dimethylethyl ester

Product 1

HCID 225729456-(tert-Butyl)indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-tert-Butyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (Prepared in Example HH; 12.0 g) in CH2Cl2 (100 mL) was cooled to 0° C. and treated with HCl gas for 10 minutes. The reaction mixture was warmed to room temperature and stirred for 1 hour. The solvents were evaporated; the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, and dried (MgSO4.) Concentration gave the title compound which was used without any further purification. MS(APCI): 176 (M+H).

Workup

  1. customwas cooled to 0° C.
  2. customThe solvents were evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3 solution and brine
  5. customdried
  6. concentration(MgSO4.) Concentration

Sources & evidence

ORD record
ord-7912b342b8fa4b6881975c0f1349c2c5
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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