Hydrochloric Acid → HCID 178518633, compound

HRID 2256996Notes

Reaction equation

HRID 2256996 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[C:9]([O:22]C)[C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)=[C:9]([OH:22])[C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 189800568-Chloro-3-methoxy-4-(4-nitrophenyl)-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine

Product 1

HCID 178518633HCID 178518633, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Chloro-3-methoxy-4-(4-nitrophenyl)-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (125 mg) was dissolved in dichloromethane (10 mL). To this was added boron tribromide (1M in dichloromethane 1 mL). This suspension was stirred for one hour. Saturated sodium bicarbonate (5 mL) was then added, and this mixture stirred for 2-3 minutes. The mixture was then adjusted to pH 3 by addition of 6N HCl. This suspension was stirred for 40 minutes, then vacuum filtered and the collected solid washed with water and crystallized from dimethylformamide (2 mL) and water (6 mL) to yield the title compound (110 mg, 91%) as an off white solid; mp 310°-312° C.; NMR: 11.90 (s,1, NH), 10.7 (broad s,1, 0H), 8.26 (dd,2, J=6.9, 2.0), 7.92 (d,1, J=8.7), 7.51 (m,3), 7.34 (dd,1, J=8.7, 2.0); MS: m/z=345(M+1). Analysis for C16H9ClN2O5 : Calculated: C, 55.75; H, 2.63; N, 8.13; Found: C, 55.49; H, 2.54; N, 8.05

Workup

  1. stirringthis mixture stirred for 2-3 minutes
  2. stirringThis suspension was stirred for 40 minutes
  3. filtrationvacuum filtered
  4. washthe collected solid washed with water
  5. customcrystallized from dimethylformamide (2 mL) and water (6 mL)

Sources & evidence

ORD record
ord-36e473e4612c477b88fae835c87e3ea7
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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