Hydrochloric Acid → HCID 5168935, compound

HRID 1077681Notes

Reaction equation

HRID 1077681 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[CH2:7]([C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH2:10][CH3:11].Cl>CO>[CH2:7]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([NH:2][OH:3])=[O:17])=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 117775Benzoic acid, 4-pentyl-, methyl esterHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 5168935HCID 5168935, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Hydroxylamine hydrochloride (17.4 g, 250 mmol.) was dissolved in AR Grade methanol (50 mL) under argon, then added to NaOMe (25% w/w in MeOH) 132 mL, 580 mmol) under argon with ice cooling. A solution of methyl 4-pentylbenzoate, prepared above (25.15 g. 123 mmol) in methanol was then added, and the reaction stirred at room temperature under N2 for 3 days. The reaction mixture was acidified to pH 6 with conc. HCl (caution!). The mixture was filtered and the filtrate evaporated to give a precipitate. This was extracted with CHCl3, the combined extracts dried (MgSO4) and the solvent evaporated. The residue was recrystallised from EtOH to give 4-pentylbenzohydroxamic acid acid as crystals, m.p. 89.9°-90.1° C. (12.35 g, 49%).

Workup

  1. additionwas then added
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customto give a precipitate
  5. extractionThis was extracted with CHCl3
  6. dry with materialthe combined extracts dried (MgSO4)
  7. customthe solvent evaporated
  8. customThe residue was recrystallised from EtOH

Sources & evidence

ORD record
ord-f71ecc0b5458421d988d8054d4241089
Source dataset
uspto-grants-1996_08
Patent number
US05545507

Reaction notes

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