Hydroquinone → N-Formylmethyl-N-(2-pyridyl)cyclohexanecarboxamide

HRID 649807Notes

Reaction equation

C[O:2][CH:3](OC)[CH2:4][N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].C1(C=CC(O)=CC=1)O.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH:3]([CH2:4][N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution consisting of 0.6 g of Compound 1A, 0.02 g of hydroquinone in 10 mL of 2 N HCl was stirred, under a nitrogen atmosphere, for 0.5 h at a temperature of 80° C. The resultant mixture was then cooled with a water bath and ice, followed by alkalinization with a 5% aqueous sodium carbonate solution (pH=9), and then by extraction with dichloromethane (2×10 mL). The obtained organic phase was dried over anhydrous sodium sulphate and evaporated to dryness. The obtained end-product material (Compound 1B; yield 68%) was suitable for use in subsequent reactions, with no additional purification processing.

Workup

extractionby extraction with dichloromethane (2×10 mL)
dry with materialThe obtained organic phase was dried over anhydrous sodium sulphate
customevaporated to dryness

Sources & evidence

ORD record: ord-f599f8dd3e8e41aa826aafda9de5093f
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271234B1

Reaction notes

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