Cyanogen Bromide → HCID 20323749, compound

HRID 839584Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[C:21]2[CH2:22][CH2:23][NH:24][CH2:25][C:20]=2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH3:18])[CH:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:4]=2[O:3]1.[N:27]#[C:28]Br.C([O-])(=O)C.[Na+]>CO>[C:28]([N:24]1[CH2:25][C:20]2[C:5]3[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH3:18])[CH:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:4]=3[O:3][C:2]([CH3:1])([CH3:26])[C:21]=2[CH2:22][CH2:23]1)#[N:27]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4.6 g (0.0129 mole) of 5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1] benzopyrano[3,4-d]pyridine, 1.38 g (0.013 mole) of cyanogen bromide, 2.13 g (0.026 mole) of sodium acetate and 35 ml of methanol was stirred at 0° C for 3 hours, and then at ambient temperature for 12 hours. After removal of the solvent under reduced pressure, water was added to the residue and the mixture was extracted with diethyl ether. The organic layer was washed with 2 N HCl, followed by saturated NaCl solution. The ether layer was separated, dried over Na2SO4 and concentrated to give 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine as a yellow oil (4.9 g, 99% yield) which crystallized upon standing.

Workup

waitat ambient temperature for 12 hours
customAfter removal of the solvent under reduced pressure, water
additionwas added to the residue
extractionthe mixture was extracted with diethyl ether
washThe organic layer was washed with 2 N HCl
customThe ether layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-f6c8641e4f6b4832a96d3c46276718dd
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04096265

Reaction notes

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