Hydrazine hydrate (1:1) → HCID 178498846, compound

HRID 2200340Notes

Reaction equation

HRID 2200340 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]2[C:9]([CH2:10][C:11](=O)[CH2:12][O:13]2)=[CH:8][CH:7]=1)=[O:4].O.[C:24]([OH:28])(=O)[CH:25]=O.O.[NH2:30][NH2:31]>C1COCC1.C(O)C>[CH3:22][C:2]([CH3:21])([CH3:1])[C:3]([NH:5][C:6]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]2[C:9]([C:10]3[CH:25]=[C:24]([OH:28])[N:30]=[N:31][C:11]=3[CH2:12][O:13]2)=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrateHCID 89705021Methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate2×

Product 1

HCID 178498846HCID 178498846, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate (Intermediate 10, 2.66 g) and glyoxylic acid monohydrate (0.802 g) in THF (6 mL) was heated in an open flask for 17 hours to give a viscous syrup which was diluted with ethanol (25 ml) and treated with hydrazine hydrate (0.471 g). The solution was stirred and heated at reflux for 45 minutes then cooled. The solid was collected by filtration to give methyl 7-(2,2-dimethylpropionylamino)-3-hydroxy-10H-9-oxa-1,2-diazaphenanthrene-8-carboxylate (1.13 g) as a sandy coloured solid.

Workup

  1. customto give a viscous syrup which
  2. temperatureheated
  3. temperatureat reflux for 45 minutes
  4. temperaturethen cooled
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-28857e686ed7429a81760e29a13fac86
Source dataset
uspto-grants-2016_06
Patent number
US09359369B2

Reaction notes

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