Ammonium Hydroxide → HCID 86745279, compound

HRID 1460608Notes

Reaction equation

HRID 1460608 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH2:12][C@H:11]1[C@:6]2([NH:17][CH3:18])[CH2:7][CH2:8][CH2:9][CH2:10]1.[NH4+].[OH-:20]>Br>[CH3:18][NH:17][C@@:6]12[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:3]=[CH:4][C:5]2=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86745280HCID 86745280, compound

Product 1

HCID 86745279HCID 86745279, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of the product from Example 133 (150 mg) in 48% aqueous HBr was heated at reflux for 2.5 hours. The reaction mixture was poured into cold aqueous NH4OH solution. The resulting solution was extracted with ethyl acetate (3×25 ml), dried (MgSO4) and filtered. Evaporation of the solvent and drying in vacuo afforded the title compound as a tan solid (90 mg, 74%), mp 191° C.

Workup

  1. temperatureat reflux for 2.5 hours
  2. extractionThe resulting solution was extracted with ethyl acetate (3×25 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-c2f25b18dc0e49b28085339a0a7c8304
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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