Acetic Acid → Methyl 4-amino-3-ethynylbenzoate

HRID 1037579Notes

Reaction equation

HRID 1037579 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]#[C:13][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.O>O1CCCC1.ClCCl>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]#[CH:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59800132HCID 59800132, compound

Product 1

HCID 640700Methyl 4-amino-3-ethynylbenzoateYield 100.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.9 g (7.7 mmol) of methyl 4-amino-3-trimethylsilylethynylbenzoate were initially charged in 20 ml of tetrahydrofuran (THF). At from 5° C. to 8° C., 8.45 ml (8.5 mmol) of tetrabutylammonium fluoride solution (1 M in THF) were added dropwise within 5 minutes. After 25 min at 2° C., 438 ml of acetic acid were added. After addition of water and extraction with dichloromethane, and after removal of the solvent, 1.35 g of methyl 4-amino-3-ethynylbenzoate were obtained. HPLC method as in example 1.

Workup

  1. customafter removal of the solvent

Sources & evidence

ORD record
ord-ed4b003ce9e24fae9f466902297c465a
Source dataset
uspto-grants-2013_10
Patent number
US08546567B2

Reaction notes

Loading…