tert-Butyl acrylate → HCID 86634101, compound

HRID 2275517Notes

Reaction equation

HRID 2275517 reaction equation
C(OC(C)(C)C)(=O)C=C.[C:10]([O:14][C:15](=[O:33])[CH:16]=[CH:17][C:18]1[CH:31]=[CH:30][C:29]2[C:20](=[C:21]([NH2:32])[C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=1)([CH3:13])([CH3:12])[CH3:11]>C(O)C>[C:10]([O:14][C:15](=[O:33])[CH2:16][CH2:17][C:18]1[CH:31]=[CH:30][C:29]2[C:20](=[C:21]([NH2:32])[C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 15458tert-Butyl acrylateHCID 86634100HCID 86634100, compound2×

Product 1

HCID 86634101HCID 86634101, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heck reaction with tert-butyl acrylate (Step 4) worked well to successfully synthesise 3-(9-amino-acridin-2-yl)-acrylic acid tert-butyl ester (Compound 6). The best condition to reduce the double bond was a catalytic hydrogenation at 3 bars in ethanol. The expected 3-(9-amino-acridin-2-yl)-propionic acid tert-butyl ester (Compound 7) was isolated by column chromatography as the major product. Another isomer and a by-product resulting in the reduction of the aromatic ring were also isolated.

Sources & evidence

ORD record
ord-73b73867c4fc48c8aaecfa031bb0d93f
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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