Phenolphthalein → HCID 123617581, compound

HRID 515651Notes

Reaction equation

HRID 515651 reaction equation
Cl.NO.C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.C[O-].[Na+].O=C1N[C@H]2CS[C@@H](CCCCCC3[O:49][N:48]=[C:47]([CH2:50][CH2:51][CH2:52][CH2:53][N:54]4[C:58]5[CH:59]=[C:60]([CH3:63])[CH:61]=[CH:62][C:57]=5[O:56][C:55]4=[O:64])[N:46]=3)[C@H]2N1>CO.C(O)C>[OH:49][N:48]=[C:47]([NH2:46])[CH2:50][CH2:51][CH2:52][CH2:53][N:54]1[C:58]2[CH:59]=[C:60]([CH3:63])[CH:61]=[CH:62][C:57]=2[O:56][C:55]1=[O:64]

Participants

7

Reactant 4

HCID 4764PhenolphthaleinHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 71536992HCID 71536992, compound

Product 1

HCID 123617581HCID 123617581, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of hydroxylamine hydrochloride salt (345 mg, 5.00 mmol) and phenolphthalein (1 crystal) in anhydrous methanol (5 ml) was stirred at reflux under an nitrogen atmosphere. Sodium methoxide was added portion-wise until a pink solution persisted (approximately 350 mg was used). The hot solution was filtered directly into a solution of compound 2 (115 mg, 0.50 mmol) in anhydrous ethanol (5 ml). The reaction mixture was stirred at reflux under a nitrogen atmosphere for 6 h. The reaction mixture was cooled, concentrated in vacuo and purified by silica gel chromatography eluting with 19:1 dichloromethane/methanol to give a brown solid (68 mg, 52%).

Workup

  1. temperatureat reflux under an nitrogen atmosphere
  2. temperatureat reflux under a nitrogen atmosphere for 6 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography
  6. washeluting with 19:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-fc65aff711ec4f47a1045928bc76d18f
Source dataset
uspto-grants-2015_08
Patent number
US09108978B2

Reaction notes

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