Hydrochloric Acid → HCID 178518631, compound

HRID 1757382Notes

Reaction equation

HRID 1757382 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9]([O:13]C)[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9]([OH:13])[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 150296358-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione

Product 1

HCID 178518631HCID 178518631, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Chloro-2,5-dihydro-2,5-dioxo-3-methoxy-1H-benz[b]azepine [Formula II: RI=R2 =R4 =H; R3Cl; R5 =CH3 ](0.0789 g, 0.332 mM) was added to a solution of 1.01 mL (1.OM, CH2Cl2) boron tribromide in 1.8 mL dry methylene chloride under nitrogen. The suspension was stirred at room temperature for 0.42 hours. The reaction mixture was poured into 7 mL of saturated aqueous sodium bicarbonate and stirred for 0.25 hours. The homogeneous solution was then adjusted to pH=5 by slow addition of concentrated hydrochloric acid. The precipitate was vacuum filtered and washed with water to give 0.0683 g (92%) of white solid which was recrystallized from 5 mL DMF and 1 mL of water. After cooling in an ice bath, solid was collected by vacuum filtration, washed with water and vacuum dried at 100° C. and 15 Pato give 0.056 g (75%) of product; mp 308.5-310.5 (dec); NMR (DMSO-d6, 300 MHz): 11.57 (s,1H, N--H), 10.86 (brs,1H, O--H), 8.04 (d,1H, Jortho =8.7 Hz), 7.54 (d,1H, Jmeta =2.0 Hz), 7.31 (dd,1H, Jortho =8.7, Jmeta =2.0 Hz), 6.41 (s,1H);

Workup

  1. stirringstirred for 0.25 hours
  2. filtrationfiltered
  3. washwashed with water

Sources & evidence

ORD record
ord-f96d6e4269664d408190fbd8f6f764ba
Source dataset
uspto-grants-1995_08
Patent number
US05446039

Reaction notes

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