Hydrochloric Acid → HCID 178513269, compound

HRID 2174358Notes

Reaction equation

HRID 2174358 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:29][OH:30].Cl>O.C1COCC1.CCO>[OH:30][NH:29][C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)=[NH:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 22915493HCID 22915493, compound

Product 1

HCID 178513269HCID 178513269, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid (2.70 g, 9.60 mmol), EtOH (10 ml), THF (15 ml), K2CO3 (3.35 g, 24.2 mmol), and hydroxylamine hydrochloride (1.50 g, 21.6 mmol) was stirred at room temperature for 3.5 d, and then at 80° C. for 24 h. Water (100 ml) and 1N HCl (50 ml) were added, and the product was isolated by filtration and washed with water. The solid was suspended in MeCN (70 ml), heated to reflux, kept at room temp overnight, filtrated off, and dried under reduced pressure to yield 3.23 g (100%) of 4-(4′-(N-hydroxycarbamimidoyl)biphenyl-4-yloxy)butyric acid.

Workup

  1. waitat 80° C. for 24 h
  2. customthe product was isolated by filtration
  3. washwashed with water
  4. temperatureheated
  5. temperatureto reflux
  6. waitkept at room temp overnight
  7. filtrationfiltrated off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-914b0635919f433f8a030bc8167fc58d
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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