Water → HCID 51039064, compound

HRID 2360085Notes

Reaction equation

HRID 2360085 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[O:7]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C:17]([NH:19][CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25](OC)=[O:26])=[CH:23][CH:22]=3)=[O:18])=[C:14]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[CH:13]=2)=[CH:8]1.O>CO.C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.C(O)(=O)C>[O:7]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]([C:17]([NH:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([NH:2][OH:3])=[O:26])=[CH:29][CH:30]=3)=[O:18])=[C:14]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[CH:13]=2)=[CH:8]1

Participants

8

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide3×HCID 67078970HCID 67078970, compound

Product 1

HCID 51039064HCID 51039064, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 4764PhenolphthaleinCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent4×

Procedure

To a solution of hydroxylamine hydrochloride (0.48 g, 7.5 mmol) and phenolphtalein (1 mg) in methanol (1.25 ml) under inert atmosphere, an aliquot of sodium methoxide in methanol (taken from a solution of 2.70 g, 50 mmol of sodium methoxide in 10 ml of methanol) was added dropwise until a permanent pink color was observed. Methyl 4-[({[5-(3-furyl)-3-(4-hydroxyphenyl)-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoate (0.52 g, 1.25 mmol) and sodium methoxide in methanol (12.5 mmol, 2.46 ml of the previously prepared solution) were subsequently added. The reaction mixture was stirred for 26 h, the formation of a dense precipitate being observed. Water (3 ml) was added, and this solution was acidified with glacial acetic acid and extracted with CH2Cl2 (3×10 ml). The combined organic fractions were dried over Na2SO4 and evaporated under reduced pressure, to obtain 0.49 g of 5-(3-furyl)-N-{4-[(hydroxyamino)carbonyl]benzyl}-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxamide: Yield 94%; m.p. 159-160° C.; IR 3406, 3243, 1626, 1526, 1268 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 11.50 (s, 1H), 11.13 (s, 1H), 9.36 (s, 1H), 8.94 (s, 1H), 8.13 (s, 1H), 7.69 (d, J=8.1 Hz, 2H), 7.67 (tb, 1H), 7.34 (t, J=5.7 Hz, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 6.93 (s, 1H), 6.74 (d, J=8.4 Hz, 2H), 6.37 (d, J=2.5 Hz, 1H), 4.41 (d, J=5.8 Hz, 2H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 164.0, 161.2, 156.3, 143.6, 142.6, 138.5, 131.2, 129.9, 127.4; 127.1, 126.8, 125.9, 121.3, 118.2, 115.1, 108.7, 108.3, 42.0.

Workup

  1. additionwas added dropwise until a permanent pink color
  2. extractionextracted with CH2Cl2 (3×10 ml)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ec2388f4e73a4457bfe0fd0bb70b1674
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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