Hydrochloric Acid → N-(2-Hydroxy-4-nitrophenyl)acetamide

HRID 1354860Notes

Reaction equation

HRID 1354860 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14]C(=O)C)(=[O:3])[CH3:2].[Li+].[OH-].Cl>CO.CCOC(C)=O>[OH:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 350142HCID 350142, compound2×

Product 1

HCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid 2-acetylamino-5-nitro-phenyl ester (416) (21 g, 88.2 mmol) was suspended in MeOH (185 mL) and 2M aqueous LiOH (185 mL) was added. An instantaneous reaction occurred, the solution turned red, everything dissolved and a slight exothermic reaction was felt by the warmth of the flask. TLC (Rf: 0.55 compared to Rf: 0.45 for compound 416 in EtOAc) after 10 minutes indicated complete hydrolysis. Addition of 1.0 M aqueous HCl (500 mL) caused the color to fade and a precipitate to form. Collection of the precipitate via vacuum filtration followed by rinsing with water (2×100 mL) and drying under high vacuum for 16 h gave the desired product (417) as a yellow powder. (17.2 g, 87.8 mmol, 99.5% yield). LC-MS was inconclusive. The product was used in the next step without further characterization

Workup

  1. customAn instantaneous reaction
  2. dissolutioneverything dissolved
  3. customa slight exothermic reaction
  4. customhydrolysis
  5. customa precipitate to form
  6. customCollection of the precipitate
  7. filtrationvia vacuum filtration
  8. washby rinsing with water (2×100 mL)
  9. customdrying under high vacuum for 16 h

Sources & evidence

ORD record
ord-ce9bc395e8884b70bc0fc7206a92da29
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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