Water → HCID 19835347, compound

HRID 478081Notes

Reaction equation

HRID 478081 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34]C)[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20]2)=[CH:15][CH:14]=1.B(Br)(Br)[Br:37].O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(O)(=O)C>[BrH:37].[OH:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[OH:34])[CH2:6][CH2:7][NH:8][CH2:9][CH:10]([OH:30])[CH2:11][O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:29])[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 25134Boron tribromideHCID 14408549HCID 14408549, compound

Product 1

HCID 19835347HCID 19835347, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-[3-[(3,4-dimethoxyphenethyl)amino]-2-hydroxypropoxy]flavone, Example 3, (5.3 g, 11.1 mmol) in dry methylene chloride (100 ml) under nitrogen at -78° C. was slowly added boron tribromide (6.3 ml, 16.7 g, 66.9 mmol) via a syringe. The cooling bath was then removed and the suspension was stirred for 1 hour. The reaction mixture was carefully decomposed by addition of a sufficient amount of water to precipitate out a brown gum leaving a clear supernatant. The liquid was decanted and the residue was washed with three portions of water. The gum was dissolved in hot isopropanol, filtered, and left to precipitate overnight. The brown solid obtained was heated in acetic acid (50 ml) and water (10 ml) to give a dark brown solution which was then treated with a few crystals of sodium dithionite to give a light tan solution. In the presence of nitrogen, the product was crystallized from the solution; 1.9 g (33%), mp 207°-210° C. (decomp).

Workup

  1. customThe cooling bath was then removed
  2. additionThe reaction mixture was carefully decomposed by addition of a sufficient amount of water
  3. customto precipitate out a brown gum
  4. customleaving a clear supernatant
  5. customThe liquid was decanted
  6. washthe residue was washed with three portions of water
  7. dissolutionThe gum was dissolved in hot isopropanol
  8. filtrationfiltered
  9. waitleft
  10. customto precipitate overnight
  11. customThe brown solid obtained
  12. customto give a light tan solution
  13. customIn the presence of nitrogen, the product was crystallized from the solution

Sources & evidence

ORD record
ord-8583474156cf40669eed811502980aa6
Source dataset
uspto-grants-1989_12
Patent number
US04889941

Reaction notes

Loading…