Benzocaine → HCID 69659124, compound

HRID 1795608Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([CH3:20])([CH3:19])[CH2:7][CH:6]=[C:5]2[CH3:21].CC([O-])(C)C.[Na+].[NH2:28][C:29]1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1(C)C=CC=CC=1>[CH2:13]([O:12][C:11]1[C:2]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=2)=[CH:3][C:4]2[C:5]([CH3:21])=[CH:6][CH2:7][C:8]([CH3:20])([CH3:19])[C:9]=2[CH:10]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 110 °C

Procedure

General Procedure P A solution of 6-bromo-7-n-hexyloxy-1,1,4-trimethyl-1,2-dihydronaphthalene (Compound 99, 0.31 g, 0.9 mmol), PdCl2(dppf)(0.070 g, 0.09 mmol), dppf (0.050 g, 0.09 mmol), NaOtBu (0.12 g, 1.3 mmol), ethyl 4-aminobenzoate (0.22 g, 1.35 mmol) and 5 mL of toluene was flushed with argon for 10 min, then stirred at 110° C. in a sealed tube for 5 d. After the reaction mixture was cooled to room temperature, the solvent was removed, and the residue was purified by flash column chromatography (hexane:ethyl acetate=4:1) to give 0.058 g (15%) of the title compound as a yellowish oil.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customthe solvent was removed
customthe residue was purified by flash column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-2d67b4b7d54a4fc9bb5fd2743756febe
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026487B2

Reaction notes

Loading…