Diethyl Malonate → 4-(6-Acetylaminoindan-1-yl)butanoic acid

HRID 1385072Notes

Reaction equation

HRID 1385072 reaction equation
[N+](C1[CH:12]=[C:11]2C(CC[CH:10]2[C:13]([OH:15])=[O:14])=CC=1)([O-])=O.[C-]#[N:17].[K+].[C:19]([O:27]CC)(=[O:26])[CH2:20][C:21](OCC)=O.[CH2:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31]1>>[C:13]([NH:17][C:36]1[CH:35]=[C:34]2[C:33]([CH2:32][CH2:31][CH:21]2[CH2:20][C:19]([OH:27])=[O:26])=[CH:38][CH:37]=1)(=[O:15])[CH3:10].[C:19]([NH:17][C:36]1[CH:37]=[C:38]2[C:33]([CH2:32][CH2:31][CH:30]2[CH2:11][CH2:10][C:13]([OH:15])=[O:14])=[CH:34][CH:35]=1)(=[O:27])[CH3:20].[C:19]([NH:17][C:36]1[CH:37]=[C:38]2[C:33]([CH2:32][CH2:31][CH:30]2[CH2:12][CH2:11][CH2:10][C:13]([OH:15])=[O:14])=[CH:34][CH:35]=1)(=[O:27])[CH3:20]

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 9032Potassium CyanideHCID 10326IndaneHCID 123184886-Nitro-2,3-dihydro-1H-indene-1-carboxylic acid

Product 3

HCID 185458434-(6-Acetylaminoindan-1-yl)butanoic acidHCID 185458992-(6-Acetylaminoindan-1-yl)acetic acidHCID 185459303-(6-Acetylaminoindan-1-yl)propanoic acid

Procedure

2-(6-acetylaminoindan-1-yl)acetic acid, 3-(6-acetylaminoindan-1-yl)propanoic acid and 4-(6-acetylaminoindan-1-yl)butanoic acid were prepared from 6-nitro-1-indanecarboxylic acid by classical chain elongations by using KCN or diethyl malonate. The methodology is described for an analogous indane serie by R. Gruber et al. Tetrahedron 1974, 30, 3605-10. Alane was used for the reduction of the intermediate carboxylic acids.

Sources & evidence

ORD record
ord-aa238566599c4600aa21593557ff5098
Source dataset
uspto-grants-2001_07
Patent number
US06262087B1

Reaction notes

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