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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 2233072
Notes
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Reaction equation

HRID 2233072 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15513Monomethyl terephthalateHCID 24813Phosphorus oxychlorideHCID 684670903-Amino-4-[methyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino]benzonitrile

Product 1

HCID 684663844-(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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

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

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. customevaporated in vacuo
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes