Hydroxylamine → HCID 58702154, compound

HRID 2357518Notes

Reaction equation

HRID 2357518 reaction equation
[F:1][C:2]1[C:9]([I:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:12][OH:13]>C(O)C>[F:1][C:2]1[C:9]([I:10])=[C:8]([CH3:11])[CH:7]=[CH:6][C:3]=1/[CH:4]=[N:12]/[OH:13]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 587021552-Fluoro-3-iodo-4-methylbenzaldehyde

Product 1

HCID 58702154HCID 58702154, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-fluoro-3-iodo-4-methylbenzaldehyde (1.26 g, 4.77 mmol) in ethanol (5 mL) at RT was treated with hydroxylamine (5 mL) (50% wt. in water) and the reaction stirred for 3 h. The volatiles were removed and the residue was treated with water (5 mL), extracted with ethyl acetate (3×15 mL). The combined ethyl acetate layers were dried and concentrated. Purification on a 40 g ISCO column (eluted with 10-50% ethyl acetate in hexanes) provided the title compound as an off-white crystalline solid. MS (ESI, pos. ion) m/z: 280.0 (M+1).

Workup

  1. customThe volatiles were removed
  2. additionthe residue was treated with water (5 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe combined ethyl acetate layers were dried
  5. concentrationconcentrated
  6. customPurification
  7. washon a 40 g ISCO column (eluted with 10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-221b588861564b4590d72dbfa7d2989b
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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