N-Methyl-4-anisidine → HCID 71735925, compound

HRID 1053567Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 6a (0.20 g, 1.46 mmol) and compound 5a (0.32 g, 1.46 mmol) were stirred in acetonitrile (10.0 mL) for 30 mins and then diisopropylethylamine was added dropwise (0.40 mL, 2.92 mmol). The reaction was then stirred at 60° C. for 12 hours and monitored by TLC. The reaction mixture was concentrated, purified by column chromatography to isolate the compound 6 as a colorless oil (0.10 g, 0.36 mmol, 25% yield). MS (ESI, positive) m/z calcd. for C16H20NO3 [M+H]+: 274.14, found: 273.96. 1H NMR (CDCl3, 400 MHz) δ 6.86 (d, J=8 Hz, 2H), 6.70-6.78 (m, 6H), 4.06 (t, J=5.6 Hz, 2H), 3.78 (s, 3H), 3.64 (t, J=5.6 Hz, 2H), 2.98 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-07d20e257ab34ef4a8c13267ae795844
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394233B2

Reaction notes

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