Sodium Hydroxide → HCID 55283162, compound

HRID 219443Notes

Reaction equation

HRID 219443 reaction equation
[C:1]1([CH:11]([NH:14]C(=O)C(Cl)(Cl)Cl)[CH:12]=[CH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH:11]([NH2:14])[CH:12]=[CH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67120506HCID 67120506, compound

Product 1

HCID 55283162HCID 55283162, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Amide 11 (3.0 g, 9.1 mmol) was dissolved in 50 ml of distillated ethanol and 50 ml of 3 M aqueous solution of NaOH was added. All was stirred at 20° C. for 24 h and evaporated to aqueous residue and 32 ml of 5 M HCl was added. It was extracted twice with 40 ml of dichloromethane. The aqueous layer was alkalified with sodium carbonate to pH=8 and extracted three times with 50 ml of diethyl-ether. Organic layers were combined and dried over anhydrous sodium sulphate. Filtration and evaporation yields 1.20 g (72%) of yellow oil; 1H NMR (CDCl3) δ: 1.72 (2H, bs, NH2), 5.18-5.24 (1H, m, CH2), 5.30-5.38 (1H+1H, m, CHCH2+ArCHNH2), 6.15-6.27 (1H, m, CHCH2), 7.42-7.60 (4H, m, ArH), 7.74-7.78 (m, 1H, ArH), 7.84-7.89 (m, 1H, ArH), 8.20 (d, 1H, J=8.3 Hz, ArH) ppm; 13C NMR (CDCl3) δ: 53.92 (CNH2), 114.28 (CH2), 123.41 (CH), 123.51 (CH), 125.55 (CH), 125.56 (CH), 126.05 (CH), 127.80 (CH), 128.92 (CH), 131.40 (C), 134.00 (C), 141.71 (CH) ppm.

Workup

  1. customevaporated to aqueous residue and 32 ml of 5 M HCl
  2. additionwas added
  3. extractionIt was extracted twice with 40 ml of dichloromethane
  4. extractionextracted three times with 50 ml of diethyl-ether
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-5d73ad7af0e448f29bf6f2c6f28c4085
Source dataset
uspto-grants-2012_06
Patent number
US08202417B2

Reaction notes

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