Indan-5-amine → HCID 69672991, compound

HRID 2276333Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]([CH:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])(=O)[CH3:12]>>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[C:14]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([O:17][CH3:18])=[O:16])[CH3:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 90496Indan-5-amine

HCID 112039Dimethyl acetylsuccinate

Product 1

HCID 69672991HCID 69672991, compoundYield 53.8%

Procedure

2,3-dihydro-1H-inden-5-amine (10 g; 75 mmol) and dimethyl acetylsuccinate (12.82 g; 68 mmol) were mixed in a flask placed in a dessicator and the homogeneous mixture was stirred under vacuum (3 mbars) for 3 days. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (0 to 20%) in heptane furnished 11.1 g (48%) of dimethyl 2-(1-(2,3-dihydro-1H-inden-5-ylamino)ethylidene)succinate as a deep orange oil.

Workup

customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (0 to 20%) in heptane

Sources & evidence

ORD record: ord-1f88a68c6d7c44149d5d980e526e5f88
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132129B2

Reaction notes

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