Hydrochloric Acid → 4-(2-Cyano-5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-5,13-diaza-benzo[4,5]-cyclohepta[1,2-b]naphthalen-12-yl)benzoic acid methyl ester

HRID 2233072Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]([CH3:25])[C:11]1[CH:20]=[CH:19][C:18]2[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1)[C:5]#[N:6].[CH3:26][O:27][C:28](=[O:38])[C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=O)=[CH:31][CH:30]=1.O=P(Cl)(Cl)Cl.Cl>O.C1(C)C=CC=CC=1>[CH3:26][O:27][C:28](=[O:38])[C:29]1[CH:37]=[CH:36][C:32]([C:33]2[C:20]3=[CH:19][C:18]4[C:17]([CH3:21])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=4[CH:12]=[C:11]3[N:10]([CH3:25])[C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[N:1]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-amino-4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzonitrile (32) (R4=CH3, 30.0 mmol), terephthalic acid monomethyl ester (30.0 mmol), POCl3 (69.0 mmol), and toluene (200 mL) is heated at 80° C. for 3 days. After cooling, the reaction mixture is treated with 1 N HCl (100 mL) and H2O (100 mL) and extracted with EtOAc. The organic layer is dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (hexane:EtOAc=5:1) to give (33) (R4=CH3, Z=H).

Workup

temperatureAfter cooling
extractionextracted with EtOAc
dry with materialThe organic layer is dried over MgSO4
customevaporated in vacuo
customThe residue is purified by flash column chromatography (hexane:EtOAc=5:1)

Sources & evidence

ORD record: ord-63aa5149f70f4844973763f8c593d416
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709470B2

Reaction notes

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