1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanol → 1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanamine

HRID 1910613Notes

Reaction equation

HRID 1910613 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11](O)[CH3:12])[C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.C1C=C[NH+:17]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH2:17])[CH3:12])[C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 587073141-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 587073381-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanamineYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethanol (155 mg, 0.77 mmol) was dissolved in 6 mL of dichloromethane. PCC (416 mg, 1.93 mmol) was added portionwise and the mixture was stirred for 16 h (reaction is likely to be completed earlier). The mixture was filtered through a plug of celite. The solvent was removed by rotary evaporation to collect the desired product (90 mg, 59% yield). 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 1H), 6.96 (d, 1H), 6.14 (s, 2H), 2.59 (s, 3H).

Workup

  1. customreaction
  2. filtrationThe mixture was filtered through a plug of celite
  3. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-de9fc5689a124a00bcafb243290c82af
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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