Ammonium Hydroxide → 3-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]aniline

HRID 601515Notes

Reaction equation

HRID 601515 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[NH4+].[OH-]>CO>[Cl:3][C:4]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 574214731-[2-(2-chloro-4-nitrophenoxy)ethyl]Pyrrolidine

Product 1

HCID 196269953-Chloro-4-[2-(pyrrolidin-1-yl)ethoxy]anilineYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (0.58 g, 15.26 mmol) to a solution of 1-[2-(2-chloro-4-nitro-phenoxy)-ethyl]-pyrrolidine (0.83 g, 3.07 mmol) and NiCl2.6H2O (1.45 g, 6.12 mmol) in MeOH (20 mL). Stir at room temperature for 2 h and add 10% NH4OH solution. Extract with CH2Cl2 and then EtOAc, combine the organics, dry, and concentrate. Purify by flash chromatography using 0-10% 2N NH3/MeOH in CH2Cl2, to give the title compound (0.5 g, 69%). MS (ES+) 241.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 6.78 (d, 1H, J=8.4 Hz), 6.72 (d, 1H, J=3.1 Hz), 6.51 (dd, 1H, J=8.4, 3.1 Hz), 4.07 (t, 2H, J=6.2 Hz), 3.47 (s, 2H), 2.90 (t, 2H, J=6.2 Hz), 2.64 (m, 4H), 1.79 (m, 4H).

Workup

  1. extractionExtract with CH2Cl2
  2. customdry
  3. concentrationconcentrate
  4. customPurify by flash chromatography

Sources & evidence

ORD record
ord-104f3882d68b4c96aff5403f81ae8c47
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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