Sodium Bicarbonate → 3-(3-Hydroxyphenyl)indoline

HRID 1489149Notes

Reaction equation

HRID 1489149 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.ClCCl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 154287243-(3-Methoxyphenyl)indolineHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 212222863-(3-Hydroxyphenyl)indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.0 g portion of the (+)-3-(3-methoxyphenyl)indoline obtained in Reference Example 4 was dissolved in 30 ml of dichloromethane, and this solution was added dropwise to 40 ml of a boron tribromide dichloromethane solution (1 mole/liter) at -70° C. After stirring the solution at room temperature overnight, ice water was added, the pH was adjusted to 9 with sodium bicarbonate, and the mixture was extracted with a chloroform/ethanol mixed solvent. After drying and concentration, ether was added to the residue to precipitate crystals which were then collected by filtration to obtain 2.7 g of 3-(3-hydroxyphenyl)indoline.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with a chloroform/ethanol mixed solvent
  3. customAfter drying
  4. concentrationconcentration, ether
  5. additionwas added to the residue
  6. customto precipitate crystals which
  7. filtrationwere then collected by filtration

Sources & evidence

ORD record
ord-084dbaa962fd4bae9ca35cf78b2914fb
Source dataset
uspto-grants-1997_10
Patent number
US05677326

Reaction notes

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