Water → 2-(2-Hydroxyethyl)indoline

HRID 443807Notes

Reaction equation

HRID 443807 reaction equation
C([BH3-])#N.[Na+].[OH:5][CH2:6][CH2:7][C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.O>C(O)(=O)C>[OH:5][CH2:6][CH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 117884632-(1H-indol-2-yl)ethanol

Product 1

HCID 130143192-(2-Hydroxyethyl)indolineYield 98.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (63 g) is added in portions to a stirred solution of 2-(2-hydroxyethyl)indole (43 g) in acetic acid (750 cc), whilst cooling the reaction mixture with a bath of cold water so as not to exceed 20° C. The mixture is stirred for 24 hours at this temperature. It is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg). The residue is taken up in a mixture of water and ice (500 cc), the resulting mixture is rendered alkaline to pH 10 with an aqueous solution of sodium hydroxide and extraction is carried out with diethyl ether (3×300 cc). The organic extracts are combined, washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). 2-(2-Hydroxyethyl)indoline (43 g) is obtained in the form of a yellow oil (mass spectrum m/e=163).

Workup

  1. customto exceed 20° C
  2. concentrationIt is then concentrated to about 100 cc at 50° C. under reduced pressure (20 mm Hg)
  3. additionThe residue is taken up in a mixture of water and ice (500 cc)
  4. extractionwith an aqueous solution of sodium hydroxide and extraction
  5. washwashed with water (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)

Sources & evidence

ORD record
ord-a3430792aea848d299914c811d77abe7
Source dataset
uspto-grants-1981_04
Patent number
US04261993

Reaction notes

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