Toluene → HCID 135974499, compound

HRID 2424958Notes

Reaction equation

HRID 2424958 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[CH2:11][CH2:12][CH3:13].Br[CH2:15][C:16](=O)[CH2:17][CH3:18].C1(C)C=CC=CC=1>O1CCOCC1>[CH2:17]([C:16]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([CH2:11][CH2:12][CH3:13])[CH:4]=2)[O:7][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 131561-Bromo-2-butanoneHCID 57845479HCID 57845479, compound

Product 1

HCID 135974499HCID 135974499, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-hydroxy-3-propylbenzamide (200.0 mg, 1.1 mmol) (Example 43), 1-bromo-2-butanone (0.19 mL, 1.7 mmol), toluene (1.5 mL), and 1,4-dioxane (1.5 mL) was heated at reflux for 8 h with a Dean-Stark trap. The solvents were evaporated. The crude product was purified on HPLC to yield a solid (124.2 mg, 48%). LC/MS m/z 232 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 9.87 (s, 1H), 7.56-7.76 (m, 3H), 6.85 (d, J=8.4 Hz, 1H), 2.46-2.56 (m, 4H), 1.52-1.61 (m, 2H), 1.18 (t, J=7.6 Hz, 3H), 0.91 (t, J=7.3 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h with a Dean-Stark trap
  3. customThe solvents were evaporated
  4. customThe crude product was purified on HPLC

Sources & evidence

ORD record
ord-7b312d4453ec4306951f57f62887280b
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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