Formaldehyde → trans-3,4-dihydro-3-hydroxy-4-[N-(2-hydroxymethyl-3-oxo-cyclopent-1-enyl)amino]-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1460619Notes

Reaction equation

HRID 1460619 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:22])[CH3:21].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)O[C:29](=[O:30])C=2C=1.C=O.[OH-].[Na+]>CC(C)=O.O>[OH:1][C@H:2]1[C@H:7]([NH:8][C:9]2[CH2:13][CH2:12][C:11](=[O:14])[C:10]=2[CH2:29][OH:30])[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 4764PhenolphthaleinHCID 14798Sodium HydroxideHCID 14301304trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(3-oxo-1-cyclopent-1-enylamino)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 14301320trans-3,4-dihydro-3-hydroxy-4-[N-(2-hydroxymethyl-3-oxo-cyclopent-1-enyl)amino]-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2,98 of the title compound of example 5 are dissolved in 150 ml of acetone and a drop of a phenolphtalein-solution and the solution is mixed with 2,5 ml of a 37% formaldehyde solution three times every hour. The pH-value of the solution is kept between 8 and 9 by controlled addition of 0,1 aq. sodium hydroxide-solution. After stirring during 5 hours the reaction solution is diluted with water and the organic components are extracted with dichloromethane. Usual work up yields white crystalls of the title compound having a m.p. of 218°-220° C. (from dichloromethane/ethanol).

Workup

  1. extractionthe organic components are extracted with dichloromethane

Sources & evidence

ORD record
ord-f7e23cbb60d94b99ae3b0bde73b548ee
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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