Tetrahydrofuran → HCID 22386478, compound

HRID 2119308Notes

Reaction equation

HRID 2119308 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8]/[CH:9]=[C:10]2\OC(=O)[C:13]3[C:18]\2=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:2]=1.[OH2:20].[NH2:21][NH2:22].[CH2:23]1COCC1>CCOC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:23])[CH2:8][C:9]2[C:10]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:13](=[O:20])[NH:22][N:21]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 70112526HCID 70112526, compound

Product 1

HCID 22386478HCID 22386478, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An emulsion of 1.2 g (4.8 mmol) E/Z-3-[3-(pyridin-3-yl)propylidene]isobenzofuran-1(3H)-one and 15 ml hydrazine hydrate in 15 ml THF is stirred for 2 h at 80° C. (oil dissolves). The cooled reaction mixture is diluted with 50 ml EtOAc, the aqueous phase separated off, extracted twice with 50 ml EtOAc and discarded. The organic phases are extracted 3 times with 20 ml 1 N HCl and likewise discarded. The combined HCl extracts are adjusted to alkaline pH with 1 N NaOH and extracted 3 times with 50 ml EtOAc each time. Drying (Na2SO4) and evaporation of the organic phases yield, after crystallization from EtOAc/DIPE, the title compound; m.p. 142° C.; 1H-NMR (CDCl3) 10.45 (s, HN), 8.47 (m, 3H), 7.8 (m, 3H), 7.53 (dt, 1H), 7.22 (dd, 1H), 2.98 (t, 2H), 2.77 (t, 2H), 2.15 (quin., 2H); FAB-MS (M+H)+=266; anal. calc. (C16H15N3O) C, 72.43%; H, 5.70%; N, 15.84%; meas. C, 72.04%; H, 5.68%; N, 15.47%.

Workup

  1. dissolution(oil dissolves)
  2. customThe cooled reaction mixture
  3. customthe aqueous phase separated off
  4. extractionextracted twice with 50 ml EtOAc
  5. extractionThe organic phases are extracted 3 times with 20 ml 1 N HCl
  6. extractionextracted 3 times with 50 ml EtOAc each time
  7. customDrying
  8. custom(Na2SO4) and evaporation of the organic phases
  9. customyield
  10. customafter crystallization from EtOAc/DIPE

Sources & evidence

ORD record
ord-48b0ada268d4401cbdf1abd57e8d58c5
Source dataset
uspto-grants-2004_02
Patent number
US06686347B2

Reaction notes

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