4-Methoxy-3-methylbenzoic Acid → 4-methoxy-3-methyl-N-(2-methylheptan-4-yl)benzamide

HRID 339346Notes

Reaction equation

HRID 339346 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][CH:14]([CH2:16][CH:17]([NH2:21])[CH2:18][CH2:19][CH3:20])[CH3:15]>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:21][CH:17]([CH2:18][CH2:19][CH3:20])[CH2:16][CH:14]([CH3:15])[CH3:13])=[O:9])=[CH:5][C:4]=1[CH3:12]

Participants

3

Reactant 2

HCID 27595834-Methoxy-3-methylbenzoic AcidHCID 144181752-Methylheptan-4-amine

Product 1

HCID 575278124-methoxy-3-methyl-N-(2-methylheptan-4-yl)benzamideYield 45%

Procedure

Prepared in a similar manner as described in example 4 using 4-methoxy-3-methylbenzoic acid and 2-methyl-4-heptanamine (example 2a). Yield: 45%. 1H NMR (500 MHz, CDCl3): δ 0.93 (m, 9H); 1.39 (m, 5H); 1.53 (m, 1H); 1.67 (m, 1H); 2.24 (s, 3H); 3.86 (s, 3H); 4.23 (m, 1H); 5.64 (d, 1H); 6.82 (d, 1H); 7.54 (s, 1H); 7.61 (d, 1H). MS (278, M+H).

Workup

  1. customPrepared in a similar manner

Sources & evidence

ORD record
ord-050792f8aeeb4615850ab0d6a15ef273
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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