N-Methylaniline → HCID 71613320, compound

HRID 1053578Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Compound 11a (0.20 g, 0.816 mmol) and compound N-methylaniline (0.176 mL, 1.63 mmol) were stirred in acetonitrile (10 mL) for 30 mins and then diisopropylethylamine (0.33 mL, 2.44 mmol) was added dropwise. The reaction was then stirred at 60° C. for 12 hours and monitored by TLC. The reaction mixture was concentrated and treated with formic acid to facilitate purification by column chromatography to isolate compound 11 as a colorless oil (0.12 g, 0.36 mmol, 46% yield). MS (ESI, positive) m/z calcd. for C17H22NO2 [M+H]+: 272.16451, found: 272.16452. 1H NMR (CDCl3, 400 MHz) δ 7.29 (t, J=7.2 Hz, 2H), 6.77-6.83 (m, 7H), 6.10 (bs, 1H), 3.92 (t, J=5.2 Hz, 2H), 3.41 (t, J=7.2 Hz, 2H), 2.97 (s, 3H), 1.70-1.81 (m, 4H).

Workup

concentrationThe reaction mixture was concentrated
additiontreated with formic acid
custompurification by column chromatography

Sources & evidence

ORD record: ord-f637f61405b544fe9e0b0b58b4af4cc0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394233B2

Reaction notes

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