Hydroxylamine → HCID 21293763, compound

HRID 620815Notes

Reaction equation

HRID 620815 reaction equation
C([O:4][N:5]([CH:9]([C:11]1[CH:12]=[CH:13][C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[CH:23]=1)[CH3:10])[C:6](=[O:8])[CH3:7])(=O)C.C(OC(=O)C)(=O)C.NO.C(N(CC)CC)C>C(Cl)Cl>[OH:4][N:5]([CH:9]([C:11]1[CH:12]=[CH:13][C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[CH:23]=1)[CH3:10])[C:6](=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21293762HCID 21293762, compound

Product 1

HCID 21293763HCID 21293763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-acetoxy-N-(1-dibenzofur-3-ylethyl) acetamide. Acetic anhydride (9.0 mL) was added to a solution of the crude hydroxylamine, prepared as in step c, and triethyl amine (12.4 mL) in methylene chloride (50 mL). The reaction was stirred overnight, then washed with cold water and 3 N HCl. The methylene chloride layer was dried (Na2SO4) and concentrated to give a yellowish oil. This residue was chromatographed on 100 g of silica gel, eluting with 20% ethyl acetate in hexanes to give the desired product.

Workup

  1. washwashed with cold water and 3 N HCl
  2. dry with materialThe methylene chloride layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give a yellowish oil
  5. customThis residue was chromatographed on 100 g of silica gel
  6. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-adea5f33ead14d32a4f1d376c0b19330
Source dataset
uspto-grants-1989_04
Patent number
US04822811

Reaction notes

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