Sodium Cyanide → HCID 69282594, compound

HRID 1293467Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13](N)=[CH:12][C:11]=3[C:7]=2[C:6]([C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1.Cl.O.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C:32]([Cu])#[N:33].[C-]#N.[Na+]>O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([C:32]#[N:33])=[CH:12][C:11]=3[C:7]=2[C:6]([C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Intermediate 30 (500 mg, 1.99 mmol) was suspended in mixture of concentrated hydrochloric acid: water (1: 1) (20 ml) and stirred at 50° C. for 30 min. The suspension was cooled to 0° C. and a solution of sodium nitrite (161 mg, 2.33 mmol) in water (2 ml) was added dropwise in 15 min. The reaction was stirred for 30 min. at 0-5° C. and then neutralized to neutral pH with saturated sodium carbonate solution The reaction suspension was then added to a pre-cooled solution of CuCN (174 mg, 1.99 mmol) and NaCN (238 mg, 4.86 mmol) in water (10 ml). The reaction was allowed to come to room temperature for 2 h. The reaction mixture was then poured into water (100 ml) and the solid was filtered and then purified by column chromatography using 15% ethyl acetate-chloroform as the eluent to obtain 250 mg of the product as white solid.

Workup

temperatureThe suspension was cooled to 0° C.
stirringThe reaction was stirred for 30 min. at 0-5° C.
waitto come to room temperature for 2 h
filtrationthe solid was filtered
custompurified by column chromatography

Sources & evidence

ORD record: ord-4aa6c62d61754db996a597fcb6aa383a
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238725B2

Reaction notes

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