Hydrochloric Acid → 9-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acid

HRID 1799869Notes

Reaction equation

HRID 1799869 reaction equation
C[O:2][C:3]([C:5]1[N:14]=[C:13]2[N:7]([CH2:8][CH2:9][O:10][C:11]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:12]=32)[CH:6]=1)=[O:4].[OH-].[Li+].Cl>O1CCCC1.O>[Br:19][C:17]1[CH:16]=[CH:15][C:12]2[C:13]3[N:7]([CH2:8][CH2:9][O:10][C:11]=2[CH:18]=1)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[N:14]=3

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58204541Methyl 9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 582043519-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acidYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid methyl ester (1.000 g, 0.003095 mol) in tetrahydrofuran (7.50 mL) and water (4.5 mL) was added lithium hydroxide (0.2964 g, 0.01238 mol). The reaction was stirred at 45° C. for 2 h. The mixture was acidified to pH=1 with 2N HCl. The resulting precipitate was filtered and rinsed with cold water to obtain 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid (860 mg) as an off-white solid. MS (ESI+) 309.0/311.0

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washrinsed with cold water

Sources & evidence

ORD record
ord-c5b5c0d39a67444baf763428ba180649
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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