2-Aminoindane → HCID 67226634, compound

HRID 244766Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4].[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]1[NH2:26]>>[OH:15][C:12]1[CH:13]=[CH:14][C:5]([C:3](=[O:4])[CH2:2][NH:26][CH:18]2[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:16])[CH:8]=[CH:7]2

Participants

Reactant 2

HCID 763102-Aminoindane

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 67226634HCID 67226634, compound

Procedure

5-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone (25 mg, 0.105 mmol) prepared from literature procedure (Yoshizaki, Shiro; Tanimura, Kaoru; Tamada, Shigeharu; Yabuuchi, Youichi; Nakagawa, Kazuyuki. J. Med. Chem. (1976), 19(9), 1138-42) is reacted neat with indan-2-ylamine (205 mg, 1.21 mmol) at 25° C. for 2 hours. The reaction mixture is purified by flash chromatography (silica, CH2Cl2/methanol 9:1). ES+ MS m/e 335 (MH+).

Workup

customThe reaction mixture is purified by flash chromatography (silica, CH2Cl2/methanol 9:1)

Sources & evidence

ORD record: ord-f379d4d12c034a16894dc167b16bdc7b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658673B2

Reaction notes

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