Sodium Hydroxide → HCID 15044890, compound

HRID 1195865Notes

Reaction equation

[C:1]([BH3-])#[N:2].[Na+].[O:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[C:18](C=O)[CH:19]=[CH:20][C:7]1=2.[OH-:23].[Na+]>C(O)(=O)C>[OH:23][NH:2][CH2:1][C:18]1[CH:19]=[CH:20][C:7]2[C:6](=[O:5])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][O:9][C:8]=2[CH:17]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Sodium cyanoborohydride (13.6 g, 0.22 mol) is added in portions to a solution of 6,11-dihydro-11-oxodibenz[b,e]oxepin-3-carboxaldehyde, oxime (11 g; 0.04 mol) in acetic acid (150 ml) at 15°-20° C. (cooling). After the mixture is stirred for 2.5 hours, an additional portion of sodium cyanoborohydride (2 g) is added and the solution is stirred for an additional 2 and 3/4 hours. The mixture is neutralized to pH -7 with 50% sodium hydroxide solution, the temperature being maintained at 65° C. The product is extracted with ethyl acetate, followed by washings with water, saturated sodium chloride solution, drying and evaporating under reduced pressure to give 13.2 g of a solid residue. The residue is flash chromatographed on silica gel with chloroform then with chloroform:methanol=95:5, as eluant to give 8.66 g (78%); 3[(hydroxyamino)methyl]dibenz[b,el]oxepin-11(6H)-one, as a solid.

Workup

temperature(cooling)
stirringthe solution is stirred for an additional 2 and 3/4 hours
extractionThe product is extracted with ethyl acetate
washfollowed by washings with water, saturated sodium chloride solution
customdrying
customevaporating under reduced pressure

Sources & evidence

ORD record: ord-d86bbcaf5b9a4dd0ab4b4f4a1fa4693d
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112846

Reaction notes

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