Water → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile

HRID 1934787Notes

Reaction equation

[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].BrN1C(=[O:24])CCC1=O.O>C(Cl)Cl>[C:1]([N:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]([OH:24])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)#[N:2]

Participants

Conditions

Temperature: 45 °C

Procedure

13.2 g (0.060 mols) of (I) are dissolved at room temperature in 80 ml of CH2Cl2 under stirring, then 11.8 g (0.066 mols) of N-bromosuccinimide of purity above 98% and 0.70 g (0.003 mols) of di-tert-butyl-peroxalate are added under stirring. The reaction mixture is subjected to mild nitrogen stream for 5 minutes, then heated to 45° C. and stirred at this temperature for 85 minutes. The resulting suspension is added with 100 ml of demineralized water and 3 grams of polyethylene glycol with average molecular weight 400, then refluxed for 5 hours under strong stirring. After decanting at 30° C., the organic phase is separated, dried over 4 g of Na2SO4, filtered and the resulting solution is concentrated to 20 ml, added with 10 ml of hexane, cooled to 0-5° C. for 2 hours and filtered to obtain 8.64 g (61%) of (VI), m.p. 110-112° C.

Workup

stirringunder stirring
stirringstirred at this temperature for 85 minutes
temperaturerefluxed for 5 hours under strong stirring
customAfter decanting at 30° C.
customthe organic phase is separated
dry with materialdried over 4 g of Na2SO4
filtrationfiltered
concentrationthe resulting solution is concentrated to 20 ml
additionadded with 10 ml of hexane
temperaturecooled to 0-5° C. for 2 hours
filtrationfiltered

Sources & evidence

ORD record: ord-7b11128e608e46afb61471f705308dd8
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384217B1

Reaction notes

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