Phenolphthalein → HCID 53894701, compound

HRID 1074921Notes

Reaction equation

C[O-].[Na+].[CH3:4][O:5][NH3+:6].[Cl-].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.[C:32]([NH:51][C:52]1[CH:56]=[C:55]([C:57](=O)[C:58]([O:60][CH3:61])=[O:59])[O:54][N:53]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CO>[C:32]([NH:51][C:52]1[CH:56]=[C:55]([C:57](=[N:6][O:5][CH3:4])[C:58]([O:60][CH3:61])=[O:59])[O:54][N:53]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of sodium methoxide in methanol is added at room temperature, until a pink color persists, to 10.3 mg. (0.12 mmol) of o-methylhydroxylamine hydrochloride in dry MeOH containing a few crystals of phenolphthalein and 3 A molecular sieves. Methyl 2-(3-tritylamino-5-isoxazolyl)-2-ketoacetate (17.8 mg., 0.04 mmol) is then added and the reaction stirred at 65° C. for 5 hours. The sieves are removed by filtration and the filtrate concentrated to dryness under reduced pressure. After chromatography on silica gel (60-200 mesh) using 5:2 hexane:EtOAc as an eluent the title compound is isolated as a mixture of syn- and anti-methyloximes (13.7 mg., 72%).

Workup

customThe sieves are removed by filtration
concentrationthe filtrate concentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-8d01e5cc0a224b6d9476987494cf80df
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04394504

Reaction notes

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