Acetic Acid → HCID 13934949, compound

HRID 2308903Notes

Reaction equation

HRID 2308903 reaction equation
[CH:1](=O)[CH3:2].Cl.[Cl:5][C:6]1[CH:11]=[C:10]([NH:12][NH2:13])[CH:9]=[CH:8][C:7]=1[CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[CH2:17][O:16]1.C([BH3-])#N.[Na+].[C:27](O)(=O)[CH3:28]>C(#N)C.CCOCC>[Cl:5][C:6]1[CH:11]=[C:10]([NH:12][N:13]([CH2:1][CH3:2])[CH2:27][CH3:28])[CH:9]=[CH:8][C:7]=1[CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[CH2:17][O:16]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 13934953HCID 13934953, compound

Product 1

HCID 13934949HCID 13934949, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Acetaldehyde (0.3 ml, 0.007 mole) was added by pipet to a stirred solution of 2-[(2-chloro-4-hydrazinophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone hydrochloride (0.8 g, 0.0026 mole) and sodium cyanoborohydride (0.16 g, 0.0026 mole), in acetonitrile 25 ml). Glacial acetic acid (2 ml) was added, and the resulting mixture stirred at ambient temperature overnight. The reaction mixture was diluted with ether (200 ml) and washed with aqueous 0.5N sodium hydroxide (50 ml), then with water (2×50 ml). The ether layer was dried and then concentrated under reduced pressure to yield a yellow oil. The oil was chromatographed on silica gel, eluting with 30:70 ethyl acetate:heptane. Appropriate fractions were combined and concentrated under reduced pressure to yield 0.24 g of 2-[[2-chloro-4-(2,2-diethylhydrazinyl)phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone as a white solid; m.p. 139°-141° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. washwashed with aqueous 0.5N sodium hydroxide (50 ml)
  2. dry with materialThe ether layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customto yield a yellow oil
  5. customThe oil was chromatographed on silica gel
  6. washeluting with 30:70 ethyl acetate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4a163b3243347179813c0f979403487
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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