4-Aminophenol → HCID 71736090, compound

HRID 1053590Notes

Reaction equation

HRID 1053590 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:11][CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:13]([O-:16])([O-])=O.[K+].[K+].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[CH3:27]N(C=O)C>>[CH2:11]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][O:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:13](=[O:16])[CH3:27])=[CH:21][CH:22]=1)[CH3:12]

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 6228DimethylformamideHCID 7093N-(2-Chloroethyl)-N-ethylanilineHCID 11430Potassium Carbonate

Product 1

HCID 71736090HCID 71736090, compoundYield 60%

Conditions

Temperature
80 °C

Procedure

Compound 3a (590 mg, 3.2 mmol), K2CO3 (887 mg, 6.4 mmol), KI (106 mg, 0.66 mmol) were mixed in DMF (50 mL). 4-aminophenol (600 mg, 5.4 mmol) was added portionwise, the reaction mixture was heated and stirred at 80° C. for 18 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography provide the compound 21 (570 mg, 1.9 mmol, 60% yield) as a pale solid. 1H NMR (CDCl3, 400 MHz) δ 7.39 (d, J=9.2 Hz, 2H), 7.26 (t, J=7.6 Hz, 2H), 6.68-6.87 (m, 5H), 4.10 (t, J=6.0 Hz, 2H), 3.72 (t, J=6.4 Hz, 2H), 3.49 (q, J=7.2, 2H), 2.16 (s, 3H), 1.21 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C18H23N2O2 [M+H]+: 299.17540, found: 299.17538.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated
  4. customthe residue was quenched with 100 mL water
  5. extractionThe mixture was then extracted with EtOAc
  6. washthe combined organic layer was washed with water
  7. dry with materialbrine and dried over Na2SO4
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2d79410f9cc64e2b9bd95ca7ebda0b61
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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