Dimethylformamide → Benzenamine, 3-ethynyl-

Temperature

45 °C

A 250 ml round bottomed flask, fitted with refrigerator, under a nitrogen stream, is loaded with 3-bromoaniline (2 ml), dimethylformamide (10 ml), trimethylsilylacetylene (3.4 ml), 1,1,3,3-tetramethyl guanidine (2.5 ml), CuCl (3.6 mg), PdCl2 (9.7 mg) triphenyl phosphine (58 mg), in this order. The mixture is heated to 55°-57° C. keeping this temperature until completion of the reaction. H2O (50 ml) and ACOEt (50 ml) are added at a temperature of 35°-30° C. The organic phase is evaporated to dryness and the residue is dissolved in CH3OH (10 ml) and 50% HCl (10 ml) is heated to 40-50° C. for two hours. Methanol is evaporated off and the residual mixture is treated with NaOH, extracted with toluene. The organic phase is dried, and the solvent removed under vacuum affording 3-amino-phenyl acetylene.

1. customA 250 ml round bottomed flask, fitted with refrigerator, under a nitrogen stream
2. temperatureThe mixture is heated to 55°-57° C.
3. customuntil completion of the reaction
4. customThe organic phase is evaporated to dryness
5. dissolutionthe residue is dissolved in CH3OH (10 ml)
6. customMethanol is evaporated off
7. additionthe residual mixture is treated with NaOH
8. extractionextracted with toluene
9. customThe organic phase is dried
10. customthe solvent removed under vacuum

ORD record

ord-2adcc09e46b340a3a767ab8884b26412

Source dataset

uspto-grants-1999_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05902902