Hydrochloric Acid → HCID 72767550, compound

HRID 2116835Notes

Reaction equation

HRID 2116835 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[N:29][OH:30])[CH2:17][O:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+].Cl>C1COCC1.O.CO>[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[N:29][OH:30])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86609832HCID 86609832, compound

Product 1

HCID 72767550HCID 72767550, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

550 mg (1.4 mmol) of methyl 4-[2-(3-tert-butyl-4-diethylaminophenyl)-2-hydroxyiminoethoxy]benzoate are dissolved in 10 ml of THF. 1 ml of methanol is added, followed by addition of 164 mg (4 mmol) of powdered sodium hydroxide and 100 μl water. The reaction medium is stirred at room temperature for 12 hours and then treated with saturated ammonium chloride solution. The aqueous phase is returned to pH 5 by adding 1N hydrochloric acid, and is extracted twice with ethyl acetate. The residue obtained is purified by chromatography on a column of silica (eluent: 80/20 and then 50/50 heptane/heptane). The final product is then recrystallized from a heptane/acetone system. A white crystalline solid is obtained (m.p.=185° C., m=245 mg, yield=44%); (1H NMR (CDCl3): 1.04-1.07 (t, 6H); 1.45 (s, 9H); 2.89 (m, 4H); 5.36 (s, 2H); 7.00-7.02 (d, J=8.8 Hz, 2H); 7.22-7.25 (d, J=8.3 Hz, 1H); 7.44-7.46 (dd, J=6.2 Hz, J′=2.06 Hz, 1H); 7.72 (d, J=2.0 Hz, 1H); 8.03-8.05 (d, J=8.74 Hz, 2H)).

Workup

  1. extractionis extracted twice with ethyl acetate
  2. customThe residue obtained
  3. customis purified by chromatography on a column of silica (eluent
  4. customThe final product is then recrystallized from a heptane/acetone system
  5. customA white crystalline solid is obtained (m.p.=185° C., m=245 mg, yield=44%)

Sources & evidence

ORD record
ord-920da6f97fa34c7eae0bdb888a682be6
Source dataset
uspto-grants-2008_10
Patent number
US07439396B2

Reaction notes

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