N-Ethylaniline → HCID 71735932, compound

HRID 1053587Notes

Reaction equation

HRID 1053587 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:4].[CH2:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:13]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)=[O:4])[CH3:14]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 81531DiisopropylethylamineHCID 2363232-chloro-N-(4-hydroxyphenyl)acetamide

Product 1

HCID 71735932HCID 71735932, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 17a (250 mg, 1.35 mmol) and N-ethylaniline (0.326 mg, 2.69 mmol) in acetonitrile (6.0 mL) was added diisopropylethylamine (0.55 mL, 4.04 mmol) dropwise. After the addition was complete, the reaction was stirred at 60° C. for 12 hours. The reaction mixture was concentrated and purified by column chromatography to isolate the compound 17 as a colorless oil (150 mg, 0.55 mmol 41% yield). MS (ESI, positive) m/z calcd. for C16H19N2O2 [M+H]+: 271.14, found: 270.95. 1H NMR (CDCl3, 400 MHz) δ 8.34 (s, 1H), 7.27-7.31 (m, 4H), 6.88 (t, J=7.2 Hz, 1H), 6.80 (t, J=8.4 Hz, 4H), 3.96 (s, 2H), 3.53 (q, J1=J2=7.2, 2H), 2.20 (s, 1H), 1.24 (t, J=6.8 Hz, 3H).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-7825033941f34439843c962c3d05bfdf
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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