Boron tribromide → HCID 178516611, compound

HRID 2260361Notes

Reaction equation

HRID 2260361 reaction equation
C[O:2][C:3]1[C:4](=[O:15])[NH:5][C:6]2[CH2:14][CH2:13][CH2:12][CH2:11][C:7]=2[C:8](=[O:10])[CH:9]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[C:4](=[O:15])[NH:5][C:6]2[CH2:14][CH2:13][CH2:12][CH2:11][C:7]=2[C:8](=[O:10])[CH:9]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10822205HCID 10822205, compound

Product 1

HCID 178516611HCID 178516611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 3-methoxy-6,7,8,9-tetrahydro-1H-1-benzazepine-2,5-dione (207 mg, 1.00 mol) in dry CH2Cl2 (2 mL, distilled from CaH2) under N2, there was added a solution of BBr3 in CH2Cl2 (2.0 mL, 1M, Aldrich) in one portion over 5 seconds at rt. A brown precipitate immediately formed. The reaction was allowed to stir under N2 at rt for 45 min. The reaction was added to saturated NaHCO3 (15 mL) and the resulting orange solution was allowed to stir for 15 min. The solution was extracted with CH2Cl2 (1×4 mL). The aqueous solution was acidified with coned HCl (pH 2), the resulting precipitate collected by filtration and washed to neutrality with water (6×2 mL). Crystallization from 95% EtOH yielded beige flakes (115 mg, 60%, pure by TLC, 1H NMR and C,H,N analysis); mp 237°-238° C. (dec.); 1H NMR (DMSO-d6) δ1.55 (m, 4H), 2.27 (m, 2H), 2.45 (m, 2H), 6.30 (s, 1H), 10.14 (bs, 1H), 10.84 (s, 1H). Anal. Calcd for C10H11NO3 : C, 62.17; H, 5.74; N, 7.25. Found: C, 62.23; H, 5.62; N, 7.26.

Workup

  1. customA brown precipitate immediately formed
  2. stirringto stir for 15 min
  3. extractionThe solution was extracted with CH2Cl2 (1×4 mL)
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed
  6. customCrystallization from 95% EtOH yielded beige flakes (115 mg, 60%, pure by TLC, 1H NMR and C,H,N analysis)

Sources & evidence

ORD record
ord-603daebc07754be899bf409fa9d0082b
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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