Benzocaine → HCID 70495644, compound

HRID 2408026Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[CH:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19])=O.O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH2:49]=[C:50]([CH3:52])[CH3:51]>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][CH:13]([C:15]1[CH:22]=[CH:21][CH:20]=[C:17]([C:18]#[N:19])[CH:16]=1)[CH2:49][C:50]2([CH3:52])[CH3:51])=[O:12])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), 3-formyl-benzonitrile (2.62 g, 20 mmol) and ytterbium(III) triflate hydrate (1.86 g, 3 mmol) in acetonitrile (150 mL) was cooled to 0° C. in a sealed reaction bottle. Then a cooled solution of isobutene (5.6 g, 100 mmol) was added into. The reaction mixture was heated to 90° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) to afford 2-(3-cyano-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.0 g, 45%) as a white solid: MS (ESI) M+1=335.3.

Workup

temperatureThe reaction mixture was heated to 90° C.
customThe solvent was removed in vacuo
customthe residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-266a92094e584abb9d23eb8144b08275
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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