HCID 13343677, compound → HCID 13343680, compound

HRID 1154587Notes

Reaction equation

HRID 1154587 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:5]=[C:4]2[CH2:17][CH:18]([C:20]([OH:22])=[O:21])[O:19][C:3]=12.[Cl:23][C:24]1C(C2C=CC=CC=2C)=CC2CC(C(O)=O)OC=2C=1Cl>>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH3:24])[C:6]=2[CH:5]=[C:4]2[CH2:17][CH:18]([C:20]([OH:22])=[O:21])[O:19][C:3]=12.[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[Cl:23])[C:6]=2[CH:5]=[C:4]2[CH2:17][CH:18]([C:20]([OH:22])=[O:21])[O:19][C:3]=12

Participants

4

Reactant 2

HCID 13343677HCID 13343677, compoundHCID 20434051HCID 20434051, compound

Product 2

HCID 13343680HCID 13343680, compoundHCID 13343681HCID 13343681, compound

Procedure

8-Chloro-5,6-dihydro-3-(o-tolyl)furo[3,2-f]-1,2-benzisoxazole-6-carboxylic acid (4e) was prepared in a fashion analogous to (4a) from (3e). A tenacious impurity resulted in the need for esterification, chromatography, and hydrolysis as with (4d). Trituration in n-hexane produced (4e) in 9.4% yield, m.p. 179°-181° C. Analysis (C17H12ClNO4) C,H,N.

Sources & evidence

ORD record
ord-f291ec5900ab4527a48bb26ea90bd829
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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