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

HRID 2190442ノート

反応式

HRID 2190442 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-9d7c02803abc4c4691af04383fdd01f5
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

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