Ethanol → HCID 178424051, compound

HRID 2260351Notes

Reaction equation

HRID 2260351 reaction equation
C[O:2][C:3]1[C:4](=[O:17])[NH:5][C:6]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1.CCO>C(Cl)Cl>[OH:2][C:3]1[C:4](=[O:17])[NH:5][C:6]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 10633269HCID 10633269, compound

Product 1

HCID 178424051HCID 178424051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-methoxy-7,9-dimethyl-1H-1-benzazepine-2,5-dione (272 mg, 1.18 mmol) in dry CH2Cl2 (3 mL, distilled from CaH2 under N2, there was added a solution of BBr3 in CH2Cl2 (3 mL, 1M, Aldrich) in one portion over 10 seconds at rt. The reaction instantaneously became homogeneous and orange, then an orange precipitate formed after a few seconds. The reaction bubbled vigorously during the addition. The reaction was allowed to stir under N2 at rt for 45 min. The reaction was added to saturated NaHCO3 (30 mL) and the resulting beige suspension was allowed to stir for 15 min to give a cloudy, yellow solution. The solution was filtered through glass wool to remove any suspended matter. The resulting solution was acidified with concd HCl (pH 2), the solid collected by filtration and washed to neutrality with water (6×5 mL). The damp filter cake was crystallized from 95% EtOH (dissolved in 20 mL, hot filtered, allowed to cool to rt) to yield yellow needles (176 mg, 69%, pure by TLC, 1H NMR and C,H,N analysis); mp 211°-213° C. (EtOH), 1H NMR (DMSO-d6) δ2.28 (s, 3H), 2.42 (s, 3H), 6.27 (s, 1H), 7.31 (s, 1H), 7.47 (s, 1H), 9.90 (s, 1H), 10.74 (bs, 1H); Anal. Calcd for C12H11NO3 : C, 66.35; H, 5.10; N, 6.45. Found: C, 66.34; H, 5.13; N, 6.48.

Workup

  1. distillationdistilled from CaH2 under N2
  2. additionthere was added a solution of BBr3 in CH2Cl2 (3 mL, 1M, Aldrich) in one portion over 10 seconds at rt
  3. customThe reaction instantaneously became homogeneous
  4. customorange, then an orange precipitate formed after a few seconds
  5. customThe reaction bubbled vigorously during the addition
  6. additionThe reaction was added to saturated NaHCO3 (30 mL)
  7. stirringto stir for 15 min
  8. customto give a cloudy, yellow solution
  9. filtrationThe solution was filtered through glass wool
  10. customto remove any suspended matter
  11. filtrationthe solid collected by filtration
  12. washwashed
  13. customThe damp filter cake was crystallized from 95% EtOH (dissolved in 20 mL, hot filtered, allowed to cool to rt)
  14. customto yield yellow needles (176 mg, 69%, pure by TLC, 1H NMR and C,H,N analysis)

Sources & evidence

ORD record
ord-18a925146b7b4a05ab65c63ddeb75a97
Source dataset
uspto-grants-1995_12
Patent number
US05476933

Reaction notes

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