N-(2-methylpropyl)hydroxylamine → HCID 86586363, compound

HRID 890631Notes

Reaction equation

HRID 890631 reaction equation
[C:1]([O:4][C:5]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2].[CH2:21]([NH:25][OH:26])[CH:22]([CH3:24])[CH3:23]>CO.Cl>[C:1]([O:4][C:5]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:8]([CH:9]=[N+:25]([CH2:21][CH:22]([CH3:24])[CH3:23])[O-:26])=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 9543329N-(2-methylpropyl)hydroxylamineHCID 15550310HCID 15550310, compound

Product 1

HCID 86586363HCID 86586363, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-acetoxy-3,5-di-tert-butylbenzaldehyde (17.0 g, 0.0615 mol) in methanol (250 mL) was added isobutylhydroxylamine (5.36 g, 0.0609 mol) and concentrated hydrochloric acid (10 drops). Using a Dean-Stark trap, the resulting solution was refluxed until no more aldehyde was detected by TLC (Rf=0.23 for product and 0.84 for starting material using 3:1 hexanes/EtOAc) The solvent was removed in vacuo and the residue was a red oil which when triturated with hexanes it turned into solid. The solid was separated and washed completely with hexanes. The titled compound was isolated in 52.3% yield as a white solid, m.p. 176.8–180.4° C.

Workup

  1. customwas removed in vacuo
  2. customtriturated with hexanes it
  3. customThe solid was separated
  4. washwashed completely with hexanes

Sources & evidence

ORD record
ord-b941c4624d204c1bb01d1b6f493b5786
Source dataset
uspto-grants-2006_02
Patent number
US06998419B2

Reaction notes

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