2-Aminobenzonitrile → HCID 18981312, compound

Reaction equation

N[C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1C(O)[CH2:13][CH:12]([OH:17])[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.C(#N)C1[C:20](=CC=CC=1)[NH2:21]>>[O:17]=[C:12]1[CH2:11][CH2:10][CH2:15][C:2]([C:3]2[C:8]([NH2:9])=[C:7]([CH:6]=[CH:5][CH:4]=2)[C:20]#[N:21])=[CH:13]1

Participants

Reactant 2

HCID 729132-Aminobenzonitrile

HCID 30728331,3-Acridinediol, 9-amino-1,2,3,4-tetrahydro-

Product 1

HCID 18981312HCID 18981312, compound

Procedure

To gain entry into the 9-amino-1,2,3,4-tetrahydroacridin-1,3-diol series, i.e., to prepare diols of formula 15, an anthranilonitrile 10 is condensed with a 5-(phenyldialkylsilyl)-1,3-cyclohexanedione 11 to afford a 3-(oxocyclohex-1-enyl)-2-aminobenzonitrile 12, which is cyclized to a 9-amino-3-(phenyldialkylsilyl)acridinone 13 and, in turn, converted to a 9-amino-3-hydroxyacridinone 14 and reduced to a diol 15.

Sources & evidence

ORD record: ord-4646dab7749e44e58394031aa1f62a31
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05210087

Reaction notes

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