Psoromic Acid → 4-Hydrazonomethyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

HRID 1692628Notes

Reaction equation

HRID 1692628 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=3[O:17][C:6]=2[C:5]([CH:24]=O)=[C:4]([OH:26])[CH:3]=1)=[O:9].O.[NH2:28][NH2:29]>C(O)C>[N:28](=[CH:24][C:5]1[C:6]2[O:17][C:16]3[C:15]([C:18]([OH:20])=[O:19])=[CH:14][C:13]([O:21][CH3:22])=[C:12]([CH3:23])[C:11]=3[O:10][C:8](=[O:9])[C:7]=2[C:2]([CH3:1])=[CH:3][C:4]=1[OH:26])[NH2:29]

Participants

4

Reactant 2

HCID 23725Psoromic AcidHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 1364111364-Hydrazonomethyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of psoromic acid (1 mmol) in ethanol (25 mL) was added hydrazine hydrate (1 mmol). The reaction was stirred for half an hour and monitored by TLC. Upon completion, all of the solvent was removed by rotary evaporation. The residue was redissolved in ethanol and dried over anhydrous magnesium sulfate, filtered, and evaporated by a rotary evaporator to yield a white solid product.

Workup

  1. customUpon completion, all of the solvent was removed by rotary evaporation
  2. dissolutionThe residue was redissolved in ethanol
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated by a rotary evaporator
  6. customto yield a white solid product

Sources & evidence

ORD record
ord-1580e3f09e85478ba1f573bb6807b48b
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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