Sodium Iodide → HCID 86752384, compound

HRID 964894Notes

Reaction equation

HRID 964894 reaction equation
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.Br[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[C:12]([C:9]1[CH:8]=[CH:7][C:6]([NH:5][CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:2]=2[O:1][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1809485HCID 1809485, compound

Product 1

HCID 86752384HCID 86752384, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4'-(2-Hydroxy-3-methoxybenzylamino)acetophenone (500 mg, 1.84 mmol) is treated with 629 mg (3.22 mmol) of ethyl 4-bromobutyrate, 764 mg (5.53 mmol) of potassium carbonate and a catalytic amount (182 mg, 1.22 mmol) of sodium iodide in 2 mL N,N-dimethylformamide as described in Preparation 3 to give 680 mg of 4-[2-[[(4-acetylphenyl)amino]methyl]-6-methoxyphenoxy]butanoic acid, ethyl ester as a light brown oil (95%). The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1730, 1660, 1600 cm-1 ; MS (CI) m/e 386 (M+H), 115; Analysis calculated for C22 H27O5N: C, 68.55; H, 7.06; N, 3.63; found: C, 68.27; H, 6.81; N, 3.54.

Sources & evidence

ORD record
ord-5c50798eff984d649cf9a7176e2c8a68
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

Loading…