3-Amino-4-hydroxybenzonitrile → 565237-26-5

HRID 2218957Notes

Reaction equation

HRID 2218957 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[Cl-].Cl[C:13](=[N+:15]([CH3:17])[CH3:16])Cl>C(Cl)Cl>[CH3:13][N:15]([CH3:17])[C:16]1[O:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2712583-Amino-4-hydroxybenzonitrileHCID 2723945Phosgeniminium chloride

Product 1

HCID 69218842565237-26-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-Amino-4-hydroxybenzonitrile (2 g, 14.9 mmol) and dichloromethylenedimethylammonium chloride (phosgene iminium chloride, 2.42 g, 14.9 mmol) in 50 mL of dry CH2Cl2 was refluxed for 6 h. After cooling the solution was extracted with EtOAc, washed with NaHCO3, brine and dried (MgSO4). The residue was crystallized in MeOH yielding 2.51 g (90%) of the title compound as a white solid. M.p.: 198-200° C., 1H NMR (CD3OD) δ 7.61 (d, 1H, J=2.8 Hz, H-4), 7.36-7.32 (m, 2H, H-6, H-7), 3.28 (s, 6H, CH3×2); 13C NMR (CD3OD) δ 164.4 (C-2), 152.2 (C-7a), 145.0 (C-3a), 125.4 (C-6), 120.0 (CN), 119.9 (C-4), 109.8 (C-7), 108.0 (C-5), 38.2 (CH3).

Workup

  1. temperaturewas refluxed for 6 h
  2. temperatureAfter cooling the solution
  3. extractionwas extracted with EtOAc
  4. washwashed with NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. customThe residue was crystallized in MeOH yielding 2.51 g (90%) of the title compound as a white solid

Sources & evidence

ORD record
ord-5ea7ecbe61ba4fbfa2936a26e31f304d
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

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