Hexan-3-amine → N-(hexan-3-yl)-4-methoxy-3-methylbenzamide

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[CH3:12].[CH3:13][CH2:14][CH:15]([NH2:19])[CH2:16][CH2:17][CH3:18]>>[CH3:13][CH2:14][CH:15]([NH:19][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH3:12])[CH:5]=1)[CH2:16][CH2:17][CH3:18]

Participants

Reactant 2

HCID 86062Hexan-3-amine

HCID 27595834-Methoxy-3-methylbenzoic Acid

Product 1

HCID 57527747N-(hexan-3-yl)-4-methoxy-3-methylbenzamide

Procedure

Prepared in a similar manner to example 4 using 4-methoxy-3-methylbenzoic acid and hexan-3-amine (example 28a). 1H NMR (500 MHz, CDCl3): δ 0.94 (m, 6H); 1.41 (m, 4H); 1.46 (m, 1H); 1.64 (m, 1H); 2.24 (s, 3H); 3.87 (s, 3H); 4.08 (m, 1H); 5.69 (d, 1H); 6.83 (d, 1H); 7.54 (s, 1H); 7.62 (d, 1H). MS (M+H, 250).

Sources & evidence

ORD record: ord-02613f52067e4b6098db4816312646f6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895050B2

Reaction notes

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