Triethylamine → N-Methyl-8-(1,3,3-trimethylbutoxy)quinolin-2-amine

HRID 1611699Notes

Reaction equation

HRID 1611699 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH:13]([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[CH2:21][N:22](CC)CC>CN1C(=O)CCC1>[CH3:21][NH:22][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH:13]([CH3:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 22254567HCID 22254567, compound

Product 1

HCID 11778029N-Methyl-8-(1,3,3-trimethylbutoxy)quinolin-2-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 7.5 mL conical microwave vessel (Personal Chemistry) equipped with a septum cap and a magnetic stirring bar was charged with 0.25 g (0.90 mmol) of 2-Chloro-8-(1,3,3-trimethylbutoxy)quinoline, NEt3 (1.26 mL) and NMP (1.26 mL). The resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (220° C. for 25 min; 300 W). Upon cooling, the residue was dissolved in a 3:1 hexanes/CH2Cl2 mixture (10 mL) and washed with H2O. The organic layer was evaporated in vacuo and the residue was purified by silica gel column chromatography (5–15% MeOH/CH2Cl2) to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 6.67–7.79 (m, 5H), 4.87 (m, 1H), 3.11 (m, 3H), 2.03 (m, 1H), 1.56 (m, 1H), 1.30 (m, 3H), 0.89 (m, 9H); MS (DCI/NH3) m/z 273 [M+H]+.

Workup

  1. customA 7.5 mL conical microwave vessel (Personal Chemistry) equipped with a septum
  2. customcap
  3. customThe resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (220° C. for 25 min; 300 W)
  4. temperatureUpon cooling
  5. washwashed with H2O
  6. customThe organic layer was evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography (5–15% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-dacb495a41e149b18782c195dca81f97
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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