Hydrochloric Acid → (2-Aminophenyl)(3-methoxyphenyl)methanone

HRID 1870729Notes

Reaction equation

O(N(C)[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7])C.Br[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1N)[O:18][CH3:19].[Li]CCCC.Cl>C1COCC1>[NH2:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[C:4]([C:15]1[CH:22]=[CH:21][CH:20]=[C:17]([O:18][CH3:19])[CH:16]=1)=[O:12]

Participants

Conditions

Temperature: -78 °C

Procedure

In a flame-dried round bottom flask, anthranilic acid N-methoxyl-N-methylamide (8.00 g, 44.4 mmol) and m-bromoanisidine (8.31 g, 44.4 g) were dissolved in 250 mL of THF and the resulting solution was cooled to -78° C. With vigorous stirring, 2 equiv of nBuLi in hexanes (55.5 mL, 1.6 M, 88.8 mmol) was added dropwise by a syringe pump at 0.6 mL/min. After 20 min, 80 mL of 1 N hydrochloric acid was carefully added, the mixture was extracted with ethyl acetate (600 mL), and the ethyl acetate was washed with water (300 mL) and brine (300 mL), dried over sodium sulfate and concentrated in vacuo. Flash chromatography with 95:5 hexanes/ethyl acetate afforded 6.92 g (69% yield) of 2-amino-3'-methoxybenzophenone as a yellow oil. 2-Amino-3'-methoxybenzophenone was converted to 2-amino-3'-hydroxybenzophenone (below) prior to characterization.

Workup

extractionthe mixture was extracted with ethyl acetate (600 mL)
washthe ethyl acetate was washed with water (300 mL) and brine (300 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9a8468b42af148ceb614fbf60629a576
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100254

Reaction notes

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