Sodium Formate → 5,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one

HRID 718050Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of title compound 85 (1.75 g, 7.15 mmol) in a solution of sodium formate (2.43 g, 35.8 mmol) in water (32 mL) was stirred at 50° C. for 8 hours and then at room temperature. The reaction mixture was filtered and the resulting solid was dissolved in THF (20 mL), diluted with ethyl acetate (200 mL) then filtered through Celite® and concentrated. The crude residue was triturated in 30% ethyl acetate in hexanes to afford title compound 86 (1.17 g, 78%) as a yellow solid. LRMS (ESI): (calc) 210.08. (found) 211.2 (MH)+. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.84 (s, 1H), 7.84 (s, 1H), 7.67 (dd, J=7.9, 1.7 Hz, 1H), 7.33 (ddd, J=8.1, 7.2, 1.8 Hz, 1H), 7.00-6.86 (m, 6H).

Workup

customat room temperature
filtrationThe reaction mixture was filtered
dissolutionthe resulting solid was dissolved in THF (20 mL)
additiondiluted with ethyl acetate (200 mL)
filtrationthen filtered through Celite®
concentrationconcentrated
customThe crude residue was triturated in 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-857a8144bb744f4db5e2bb681f562b61
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Reaction notes

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