HCID 15020499, compound → HCID 15020501, compound

HRID 1090841Notes

Reaction equation

HRID 1090841 reaction equation
[C:1]1([C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]=[N:9][C:10]2[N:15]=[N:14][C:13]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.O1CCCC1.[Pd]>[OH:21][CH:18]([CH2:19][OH:20])[CH2:17][O:16][C:13]1[N:14]=[N:15][C:10]([NH:9][NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 1

HCID 15020499HCID 15020499, compound

Product 1

HCID 15020501HCID 15020501, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of (RS)-3-[(6-triphenylmethylazo-3-pyridazinyl)oxy]-1.2-propanediol (5.45 g) in 95% ethanol (100 ml) and tetrahydrofuran (50 ml) containing 5% palladium on charcoal (1.1 g) hydrogen was bubbled, at room temperature, for 16 hours. Removal of the catalyst and evaporation of the solvent gave a residue which was crystallized from 2-propanol to yield 3.2 g of the title compound. m.p. 174°-176° C. Mass spectrum (E.I. 70 eV, 1.5 mA), m/z=412 (M-N2H2)+, 338 (M-C3H8N2O2)+, 243 (Ph3C)+.

Workup

  1. customwas bubbled, at room temperature, for 16 hours
  2. customRemoval of the catalyst and evaporation of the solvent
  3. customgave a residue which
  4. customwas crystallized from 2-propanol

Sources & evidence

ORD record
ord-b17f6d33548c4aca896a8fac76ace0f1
Source dataset
uspto-grants-1992_01
Patent number
US05082939

Reaction notes

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