Ethanol → HCID 59242039, compound

HRID 1876179Notes

Reaction equation

HRID 1876179 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:22]([OH:24])[CH3:23]>Cl>[CH2:22]([O:24][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:23]

Participants

4

Reactant 2

HCID 702EthanolHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 59242039HCID 59242039, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine 3.98 g (20.0 mmol) in ethanol 4 mL and concd HCl 3 mL was stirred at room temperature for 14 h. After removal of ethanol, the residue was dissolved in ethyl acetate, and the organic solution was washed with water, satd Na2CO3, and dried over anhydrous MgSO4. After removal of solvent under reduced pressure, the crude product was purified by MPLC (SiO2, EtOAc 0˜100% in hexanes) to give the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.91-7.94 (m, 1H), 7.54-7.61 (m, 2H), 7.25-7.29 (m, 2H), 7.12-7.16 (m, 1H), 6.90-6.94 (m, 1H), 4.29 (q, J=7.0 Hz, 2H), 3.84 (s, 3H), 3.60 (s, 3H), 1.34 (t, J=7.0 Hz, 3H); LC-MS (ESI+; 310 ([M+H]+)).

Workup

  1. customAfter removal of ethanol
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe organic solution was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. customAfter removal of solvent under reduced pressure
  6. customthe crude product was purified by MPLC (SiO2, EtOAc 0˜100% in hexanes)

Sources & evidence

ORD record
ord-376d450daa314b10b92b3d4cbb6415f4
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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