Water → Indoline-4-ol

HRID 710391Notes

Reaction equation

HRID 710391 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[BH3-]C#N.[Na+].O>CC(O)=O>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 754211H-indol-4-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3021054Indoline-4-olYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-hydroxyindole (0.16 g; 1.2 mmol) in AcOH (6 ml) was treated with NaBH3CN (0.23 g; 3.6 mmol), at rate keeping the temperature below 15° C. The mixture was then stirred for 1 h at room temperature and H2O (0.4 ml) was added and solvents removed in vacuo. The residue was diluted to 15 ml with EtOAc, washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.16 g; 99%) as creamy solid. 1H-NMR (CDCl3) 2.93 (tr, 2H, J=8.4 Hz); 3.58 (tr, 2H, J=8.4 Hz); 3.74 (broad s, 2H); 6.17 (d, 1H, J=8 Hz); 6.26 (d, 1H, J=7.72 Hz); 6.88 (tr, 1H, J=7.85 Hz).

Workup

  1. customthe temperature below 15° C
  2. customsolvents removed in vacuo
  3. additionThe residue was diluted to 15 ml with EtOAc
  4. washwashed with 5% NaHCO3, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-298baf2d34854abf87182985027a4447
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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