5-Amino-2-methylphenol → 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide

HRID 2190442Notes

Reaction equation

HRID 2190442 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:14][CH2:13]1)#[N:11].C(Cl)(=O)C(Cl)=O.C(=O)([O-])O.[Na+]>O.O1CCCC1.CN(C)C=O>[C:10]([C:12]1([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=2)=[O:19])[CH2:13][CH2:14]1)#[N:11]

Participants

8

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Product 1

HCID 673125573-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamideYield 87.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using 5-amino-2-methylphenol (6.00 g, 48.5 mmol), 3-(1-cyanocyclopropyl)benzoic acid (6.00 g, 48.5 mmol) produced in Example A1(iii), oxalyl chloride (6.40 mL, 73.0 mmol), N,N-dimethylformamide (40 μL), tetrahydrofuran (250 mL), sodium hydrogencarbonate (6.20 g, 73.0 mmol) and water (60 mL) as starting materials, and in the same manner as in Example A32(i), the title compound (12.4 g, 87%) was obtained as a white powder. The title compound was washed with a mixed solvent of ethyl acetate and hexane.

Sources & evidence

ORD record
ord-9d7c02803abc4c4691af04383fdd01f5
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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