Hydrochloric Acid → 3-phenyl-2,3-dihydro-1H-indole

HRID 1489143Notes

Reaction equation

HRID 1489143 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9](C(=O)[C@H]3CCCN3S(C3C=CC(C)=CC=3)(=O)=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)(=O)C>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15428730HCID 15428730, compound

Product 1

HCID 109323533-phenyl-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 5.0 g portion of the 3-phenyl-1-(N-tosyl-D-prolyl)-indoline obtained above was suspended in a mixed solution of 40 ml acetic acid and 15 ml concentrated hydrochloric acid, and heated under reflux for 6 hours. The reaction solution was concentrated under reduced pressure and washed with toluene, and then the aqueous layer was made basic with an aqueous sodium hydroxide solution and extracted with diethyl ether. The extract was dried and concentrated to obtain 1.52 g of (+)-3-phenylindoline as yellow crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washwashed with toluene
  5. extractionextracted with diethyl ether
  6. customThe extract was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fad04febd0cd4baf95a9e62a5d0fe83c
Source dataset
uspto-grants-1997_10
Patent number
US05677326

Reaction notes

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