6,7-Dichloro-2-ethyl-2-(n-propyl)-1-hydroxyindan-5-ylacetamide → 4-(6,7-Dichloro-2-ethyl-2-methyl-1-hydroxyindan-5-yl)-3-hydroxy-3-pyrroline-2,5-dione

HRID 66690Notes

Reaction equation

HRID 66690 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]([CH3:16])[CH3:15])([CH3:13])[CH:8]2[OH:12])=[CH:4][C:3]=1[CH2:17][C:18]([NH2:20])=[O:19].[Cl:21][C:22]1[C:30]([Cl:31])=[C:29]2[C:25]([CH2:26][C:27]([CH2:34][CH3:35])([CH3:33])[CH:28]2[OH:32])=[CH:24][C:23]=1[CH2:36][C:37]([NH2:39])=[O:38].[Cl:40][C:41]1[C:49]([Cl:50])=[C:48]2[C:44]([CH2:45][C:46]([CH2:55][CH3:56])([CH2:52][CH2:53][CH3:54])[CH:47]2[OH:51])=[CH:43][C:42]=1[CH2:57][C:58]([NH2:60])=[O:59].C([O:63][C:64](=[O:70])[C:65]([O:67]CC)=[O:66])C.CC(C)([O-])C.[K+]>>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]([CH3:16])[CH3:15])([CH3:13])[CH:8]2[OH:12])=[CH:4][C:3]=1[C:17]1[C:18](=[O:19])[NH:20][C:64](=[O:63])[C:65]=1[OH:66].[Cl:21][C:22]1[C:30]([Cl:31])=[C:29]2[C:25]([CH2:26][C:27]([CH2:34][CH3:35])([CH3:33])[CH:28]2[OH:32])=[CH:24][C:23]=1[C:36]1[C:37](=[O:38])[NH:39][C:64](=[O:70])[C:65]=1[OH:67].[Cl:40][C:41]1[C:49]([Cl:50])=[C:48]2[C:44]([CH2:45][C:46]([CH2:55][CH3:56])([CH2:52][CH2:53][CH3:54])[CH:47]2[OH:51])=[CH:43][C:42]=1[C:57]1[C:58](=[O:59])[NH:60][C:64](=[O:63])[C:65]=1[OH:66]

Participants

7

Reactant 4

HCID 540838716,7-Dichloro-2-ethyl-2-(n-propyl)-1-hydroxyindan-5-ylacetamideHCID 541928086,7-Dichloro-2-(i-propyl)-2-methyl-1-hydroxyindan-5-ylacetamideHCID 542378066,7-Dichloro-2-ethyl-2-methyl-1-hydroxyindan-5-ylacetamideHCID 86738520HCID 86738520, compound

Product 3

HCID 546899554-(6,7-Dichloro-2-ethyl-2-methyl-1-hydroxyindan-5-yl)-3-hydroxy-3-pyrroline-2,5-dioneHCID 546899584-[6,7-Dichloro-2-(i-propyl)-2-methyl-1-hydroxyindan-5-yl]-3-hydroxy-3-pyrroline-2,5-dioneHCID 546899594-[6,7-Dichloro-2-ethyl-2-(n-propyl)-1-hydroxyindan-5-yl]-3-hydroxy-3-pyrroline-2,5-dione

Procedure

When 6,7-dichloro-2-(i-propyl)-2-methyl-1-hydroxyindan-5-ylacetamide, 6,7-dichloro-2-ethyl-2-methyl-1-hydroxyindan-5-ylacetamide, and 6,7-dichloro-2-ethyl-2-(n-propyl)-1-hydroxyindan-5-ylacetamide are utilized as starting materials in the diethyloxalate/potassium t-butoxide reaction there are obtained 4-[6,7-dichloro-2-(i-propyl)-2-methyl-1-hydroxyindan-5-yl]-3-hydroxy-3-pyrroline-2,5-dione, 4-(6,7-dichloro-2-ethyl-2-methyl-1-hydroxyindan-5-yl)-3-hydroxy-3-pyrroline-2,5-dione, and 4-[6,7-dichloro-2-ethyl-2-(n-propyl)-1-hydroxyindan-5-yl]-3-hydroxy-3-pyrroline-2,5-dione.

Sources & evidence

ORD record
ord-cabe67cb34cb40489d9e816734a74467
Source dataset
uspto-grants-1982_08
Patent number
US04342776

Reaction notes

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