Phenylhydrazine → HCID 135487800, compound

HRID 2305428Notes

Reaction equation

HRID 2305428 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]2[C:9]([C:11]3[C:30]([C:31](=[O:32])[C:5]2=[CH:4][C:3]=1[OH:36])=[C:29]([OH:33])[C:14]1[C:15]2[C:20]([CH2:21][CH2:22][C:13]=1[C:12]=3[O:34][CH3:35])=[CH:19][C:18]1[CH:23](O)[O:24][C:25](=O)[C:17]=1[C:16]=2[OH:28])=[O:10].[C:37]1([NH:43][NH2:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)(=O)C>[C:37]1([N:43]2[C:25](=[O:24])[C:17]3[C:16]([OH:28])=[C:15]4[C:14]5[C:13]([CH2:22][CH2:21][C:20]4=[CH:19][C:18]=3[CH:23]=[N:44]2)=[C:12]([O:34][CH3:35])[C:11]2[C:9](=[O:10])[C:6]3[C:5](=[CH:4][C:3]([OH:36])=[C:2]([CH3:1])[C:7]=3[OH:8])[C:31](=[O:32])[C:30]=2[C:29]=5[OH:33])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 460028HCID 460028, compound

Product 1

HCID 135487800HCID 135487800, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 5% mixture of madurahydroxylactone in glacial acetic acid is mixed with 2 mole equivalents of phenylhydrazine and boiled under reflux for 30 min. The reaction mixture is then left to stand at room temperature for about 12 hours. The red solid which has crystallized out is filtered off with suction, washed with glacial acetic acid and dried. The crude product is extracted with tetrahydrofuran (THF) in a Soxhlet. On cooling, the product crystallizes out and is filtered off with suction and dried. The yield is about 83% of theory.

Workup

  1. temperatureunder reflux for 30 min
  2. waitThe reaction mixture is then left
  3. customThe red solid which has crystallized out
  4. filtrationis filtered off with suction
  5. washwashed with glacial acetic acid
  6. customdried
  7. extractionThe crude product is extracted with tetrahydrofuran (THF) in a Soxhlet
  8. temperatureOn cooling
  9. customthe product crystallizes out
  10. filtrationis filtered off with suction
  11. customdried

Sources & evidence

ORD record
ord-a4d1ef790d654f17889c34218376c92e
Source dataset
uspto-grants-2002_08
Patent number
US06440968B1

Reaction notes

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