Diethyl Ether → 3860-58-0

HRID 244806Notes

Reaction equation

HRID 244806 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].CCO[CH2:12][CH3:13]>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:12]=1[CH:13]=[N:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 58012-Aminophenol

Product 1

HCID 1354968143860-58-0

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Aminophenol (1.09 g, 10 mmol) was dissolved in ether (20 mL) and DCM (5 mL). 2-pyridinecaroxaldehyde (0.95 mL, 10 mmol) was added to the above solution. The reaction mixture was stirred at room temperature for 17 h; precipitate was formed. The light yellow solid (1.52 g, 77%) was filtered and dried. 1H (CDCl3) δ 8.85 (s, 1H), 8.72 (d, J=3 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 7.84 (t, J=7.5 Hz, 1H), 7.39 (t, J=7.5 Hz, 1H), 7.31 (bs, 1H), 7.25 (t, J=9 Hz, 1H), 7.04 (d, J=6 Hz, 1H), 6.94 (t, J=7.5 Hz, 1H), MS (M+H) 199.

Workup

  1. addition2-pyridinecaroxaldehyde (0.95 mL, 10 mmol) was added to the above solution
  2. customprecipitate was formed
  3. filtrationThe light yellow solid (1.52 g, 77%) was filtered
  4. customdried

Sources & evidence

ORD record
ord-1b25f7a0c3344591ad8aacce76bdf4ae
Source dataset
uspto-grants-2014_02
Patent number
US08658677B2

Reaction notes

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