P-Anisidine → HCID 71735773, compound

HRID 1053565Notes

Reaction equation

HRID 1053565 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 71735773HCID 71735773, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-methoxy-aniline (124 mg, 1.0 mmol) and compound 5a (200 mg, 0.92 mmol) were reacted in acetonitrile (10.0 mL) for 30 mins and diisopropylethylamine was added (0.28 mL, 2.0 mmol) dropwise. After the addition was complete, the reaction was stirred at 60° C. for 12 hours. The reaction mixture was concentrated, purified by column chromatography to isolate the compound 5 as a colorless oil (45 mg, 0.17 mmol, 19% yield). MS (ESI, positive) m/z calcd. for C15H18NO3 [M+H]+: 260.13, found: 259.94. 1H NMR (CDCl3, 400 MHz) δ 6.66-6.84 (m, 8H), 4.45 (bs, 1H), 4.12 (t, J=5.2 Hz, 2H), 3.89 (bs, 1H), 3.77 (s, 3H), 3.47 (t, J=5.2 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-36ad62cb4714474696c84ba12c75f8a0
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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