Sodium Hydroxide → HCID 178517567, compound

HRID 430597Notes

Reaction equation

HRID 430597 reaction equation
Cl[C:2]1[C:11]2[CH2:12][NH:13][C:14](=[O:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-:16].[Na+]>Cl>[OH:16][C:2]1[C:11]2[CH2:12][NH:13][C:14](=[O:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86757613HCID 86757613, compound

Product 1

HCID 178517567HCID 178517567, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

8 g (24.9 mmoles) of Compound 3 was dissolved in 1 litre of 1N HCl and heated to 80° C. for 4 h with stirring. The reaction mixture was then cooled to 0° C., brought to pH 9 with 5N NaOH and extracted with chloroform. The organic extracts were dehydrated with anhydrous sodium sulphate, filtered and evaporated at reduced pressure to give 7 g of Compound 5 (yield 88%). Crystallization from ethyl acetate, gave a pure compound which melted at 245-246° C. 1H NMR (CDCl3): 1.46-1.61 (m, 4H), 2.16-2.23 (m, 5H), 2.43-2.58 (m, 2H), 3.27 (m, 2H), 4.35 (s, 2H), 4.61 (m, 1H), 7.28-7.36 (m, 2H), 7.55 (m, 1H), 8.84 (d, j=8.2, 1H), 10.63 (br s, 1H), MS: m/z 323 (M+, 28).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. extractionextracted with chloroform
  3. filtrationfiltered
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-b4282314bd8b4cdf9167eda068d8370c
Source dataset
uspto-grants-2001_11
Patent number
US06323216B1

Reaction notes

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