Water → 5-(Benzyloxy)-1H-indol-1-amine

HRID 1029709Notes

Reaction equation

HRID 1029709 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[NH2:20]OS(O)(=O)=O.O>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([NH2:20])[CH:13]=[CH:12]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 149882975-(Benzyloxy)-1H-indol-1-amineYield 133.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-phenylmethoxyindole (50 g) in 300 ml of dimethylformamide at ice bath temperature was added milled potassium hydroxide (62.72 g). Then hydroxylamine-O-sulfonic acid (32.93 g) was added portionwise, keeping the internal temperature below 20° C. After the addition was complete, the mixture was stirred for one hour, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4). After filtration, the solvent was evaporated to yield an oil (71 g), which was eluted with dichloromethane on silica gel columns via HPLC. The desired fractions were concentrated to yield a solid (21.15 g). Of this material, 3.0 g was triturated with ether to yield a solid, 2.4 g, m.p. 126°-128° C.

Workup

  1. customthe internal temperature below 20° C
  2. additionAfter the addition
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (sat. NaCl
  6. filtrationAfter filtration
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4075b2b1b94d4663b32819e722d4f79a
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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