Hydrochloric Acid → HCID 22319294, compound

HRID 497515Notes

Reaction equation

HRID 497515 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>CCO.O>[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:23])=[O:3])=[CH:6][CH:7]=1)(=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 289856ethyl 4-(decanoylamino)benzoate

Product 1

HCID 22319294HCID 22319294, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(Scheme 3, Compound I) To a solution of 4-decanoylamino-benzoic acid ethyl ester (2.0 g, 6.6 mmol) in EtOH (30 mL) was added NaOH (10 N, 6 mL, 60 mmol). The resulting mixture was stirred at rt for 3 hours, diluted with H2O (30 mL), acidified to pH˜1.0 using HCl (6N). The precipitates were filtered off by filter paper, washed by H2O and hexanes. This compound was obtained as a white solid. (1.8 g, 6.5 mmol, 98% yield). 1H NMR (DMSO-d6) δ 9.91 (br. s, 1H), 7.76 (d, 2H, J=8.7 Hz), 6.50 (d, 2H, J=8.7 Hz), 2.29 (t, 2H, J=7.5 Hz), 1.57 (m, 2H), 1.25 (m, 12H), 0.85 (t, 3H, J=6.9 Hz). Mass Spec: 278.21 (MH+).

Workup

  1. filtrationThe precipitates were filtered off
  2. filtrationby filter paper
  3. washwashed by H2O and hexanes
  4. customThis compound was obtained as a white solid

Sources & evidence

ORD record
ord-940fbf8b28d143eca84ada0d6a06ef01
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

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