Diethylamine → HCID 58112801, compound

HRID 919202Notes

Reaction equation

HRID 919202 reaction equation
Cl[CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>C(#N)C>[CH2:12]([N:14]([CH2:2][C:3]1[CH:10]=[C:7]([CH:8]=[O:9])[C:6]([OH:11])=[CH:5][CH:4]=1)[CH2:15][CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 3352915-(Chloromethyl)-2-hydroxybenzaldehyde

Product 1

HCID 58112801HCID 58112801, compoundYield 150.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(chloromethyl)salicylaldehyde (14)(345 mg, 2 mmol) in acetonitrile (70 mL), diethylamine (0.21 mL, 2 mmol) was added and the mixture refluxed overnight. Then, the solvent was evaporated to give compound 15 (625 mg, 99%) as a yellow oil. □max 3383, 2648 and 1653 cm−1. 1H-NMR δH 1.37 (6H, t, J=7.2 Hz, 2×CH2CH3), 3.43 (4H, q, J=7.2 Hz, 2×CH2CH3), 4.09 (2H, s, CCH2N), 7.05 (1H, d, J=8.6 Hz, HAr), 8.03 (1H, d, J=8.6 Hz, HAr), 8.14 (1H, s, HAr), 9.98 (1H, s, CHO), 12.32 (1H, br s, OH). 13C-NMR δC 11.4, 46.4, 56.0, 118.8, 121.3, 136.7, 139.0, 162.7, 196.5. m/z(ESI) 208 (MH+, 100), 293 (30), 317 (10). HRMS (ESI): Calculated for M+ (C12H17NO2+) 208.1338. Found 208.1355.

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThen, the solvent was evaporated

Sources & evidence

ORD record
ord-bc2e5bd5df044c16a3f21f76cb43131d
Source dataset
uspto-grants-2016_03
Patent number
US09273024B2

Reaction notes

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