Hydrochloric Acid → HCID 178516612, compound

HRID 2260363Notes

Reaction equation

HRID 2260363 reaction equation
C[O:2][C:3]1[C:4](=[O:17])[NH:5][C:6]2[CH2:14][CH:13]([Cl:15])[CH:12]([Cl:16])[CH2:11][C:7]=2[C:8](=[O:10])[CH:9]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[OH:2][C:3]1[C:4](=[O:17])[NH:5][C:6]2[CH2:14][CH:13]([Cl:15])[CH:12]([Cl:16])[CH2:11][C:7]=2[C:8](=[O:10])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19710537HCID 19710537, compound

Product 1

HCID 178516612HCID 178516612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 3-methoxy-7,8-dichloro-6,7,8,9-tetrahydro-1H-1-benzazepine-2,5-dione (100 mg, 362 μmol) in dry CH2Cl2 (2 mL, distilled from CaH2) under N2 there was added a solution of BBr3 in CH2Cl2 (1.0 mL, 1M, Aldrich) in one portion over 5 seconds at ft. A greenish yellow 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 beige suspension was allowed to stir for 15 min. The suspension was acidified with concentrated HCl (pH 2), allowed to stir for 15 rain at rt, the solid collected by filtration and washed to neutrality with water (6×2 mL). Crystallization from 95% EtOH (dissolved in 75 mL, hot filtered (Whatman #2), concd to 30 mL, allowed to cool to rt) yielded a beige amorphous solid (68 mg, 71%, >98% pure by 1H NMR, pure by C,H,N analysis); mp 246°-248° C. (dec.); 1H NMR (DMSO-d6) δ2.70 (dd, J= 18.2, 5.6 Hz, 1H), 2.91 (dd, J=18.9, 5.4 Hz, 1H), 3.06 (dd, J=18.3, 4.8 Hz, 1H), 3.26 (dd, J=18.8, 4.6 Hz, 1H), 4.57 (m, 2H), 6.34 (s, 1H), 10.46 (s, 1H), 11.11 (s, 1H). Anal. Calcd for: C, 45.83, H, 3.46, N, 5.34. Found: C, 46.02; H, 3.54; N, 5.26.

Workup

  1. customA greenish yellow precipitate immediately formed
  2. stirringto stir for 15 min
  3. stirringto stir for 15 rain at rt
  4. filtrationthe solid collected by filtration
  5. washwashed
  6. customCrystallization from 95% EtOH (dissolved in 75 mL, hot filtered (Whatman #2), concd to 30 mL, allowed to cool to rt)
  7. customyielded a beige amorphous solid (68 mg, 71%, >98% pure by 1H NMR, pure by C,H,N analysis)

Sources & evidence

ORD record
ord-cc707ad0d0c640eba1a7383b9cf546e1
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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