Hydrochloric Acid → 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide dihydrochloride

HRID 1629341Notes

Reaction equation

C(OC([NH:8][N:9]([C:13]([C:15]1[N:24]=[C:23]2[N:17]([CH2:18][CH2:19][O:20][C:21]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:22]=32)[CH:16]=1)=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.[ClH:30].O1CCOCC1>CO>[ClH:30].[ClH:30].[CH:10]([N:9]([C:13]([C:15]1[N:24]=[C:23]2[N:17]([CH2:18][CH2:19][O:20][C:21]3[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:22]=32)[CH:16]=1)=[O:14])[NH2:8])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of N′-(8-bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carbonyl)-N′-isopropyl-hydrazinecarboxylic acid tert-butyl ester (2.71 g, 5.83 mmol) in methanol (52 mL) was treated with 4N HCl in dioxane (5.83 mL, 23.3 mmol). The reaction mixture was stirred at 50° C. overnight before the reaction was concentrated in vacuo and the resultant residue triturated with diethyl ether to give 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide dihydrochloride as a pale yellow foam (2.69 g, quantitative yield). LCMS RT=4.17 min, [M+H]+=365/367

Workup

concentrationwas concentrated in vacuo
customthe resultant residue triturated with diethyl ether

Sources & evidence

ORD record: ord-a32a92c8277e420c99caed6662210dbb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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