Triethylamine → HCID 72490849, compound

HRID 2262423Notes

Reaction equation

HRID 2262423 reaction equation
[C:1]([N:5]([C:22](=[O:31])[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[NH:6][C:7]([C:9]1[CH:20]=[CH:19][C:12]2[O:13][CH2:14][CH:15]([CH:17]=O)[O:16][C:11]=2[C:10]=1[CH3:21])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:40][OH:41]>CO>[C:1]([N:5]([C:22](=[O:31])[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[NH:6][C:7]([C:9]1[CH:20]=[CH:19][C:12]2[O:13][CH2:14][CH:15]([CH:17]=[N:40][OH:41])[O:16][C:11]=2[C:10]=1[CH3:21])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10320145HCID 10320145, compound

Product 1

HCID 72490849HCID 72490849, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 mL round bottom flask, containing 100 mg (0.24 mm) of 3,5-dimethyl-benzoic acid N-tert-butyl-N′-(3-formyl-5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazide, added 0.50 g of triethylamine, 70 mg (1 mm) of hydroxylamine hydrochloride and 25 mL of methanol. The reaction mixture was refluxed for 1 hour. The methanol was removed on a rotary evaporator and the residue was dissolved with chloroform and dilute HCl and transferred to a separatory funnel. The chloroform extract was dried and evaporated to dryness. The residue was chromatographed on silica and the product eluted with 40% ethyl acetate in hexane. Evaporation of solvent yielded 85 mg of 3,5-dimethyl-benzoic acid N-tert-butyl-N′-[3-(hydroxyimino-methyl)-5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl]-hydrazide. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.7 (s, 1H), 7.4 (d, 1H), 7.05 (s, 2H), 6.95 (s, 1H), 6.55 (d, 1H), 6.15 (m, 1H), 4.8 (m, 1H), 4.0-4.4 (m, 4H), 2.248 (s, 6H), 1.915 (s, 3H), 1.574 (s, 9H); TLC: Rf=0.40 (1:1 ethyl acetate:hexane).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customThe methanol was removed on a rotary evaporator
  3. dissolutionthe residue was dissolved with chloroform and dilute HCl
  4. customtransferred to a separatory funnel
  5. extractionThe chloroform extract
  6. customwas dried
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica
  9. washthe product eluted with 40% ethyl acetate in hexane
  10. customEvaporation of solvent

Sources & evidence

ORD record
ord-9581023c80304768a6af54ae008d9767
Source dataset
uspto-grants-2010_12
Patent number
US07851220B2

Reaction notes

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