Nitric Acid → Methyl 4-acetamido-5-chloro-2-methoxy-3-nitrobenzoate

HRID 39661Notes

Reaction equation

HRID 39661 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7](=[O:21])[C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:10][C:9]=1[O:19][CH3:20]>CCOC(C)=O>[CH3:5][O:6][C:7](=[O:21])[C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([NH:15][C:16](=[O:18])[CH3:17])=[C:10]([N+:1]([O-:4])=[O:2])[C:9]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 77721Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Product 1

HCID 10402690Methyl 4-acetamido-5-chloro-2-methoxy-3-nitrobenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Fuming nitric acid (33 mL) was added dropwise at 20° C. to compound 10 (13.0 g, 0.05 mol) over 15 min. After stirring for an additional 10 min at that temperature, the mixture was poured into ice water and EtOAc (100 mL) was added. After separating the organic phase, the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4 and concentrated. Drying under hv yielded 14.0 g (91%) of 11 as a beige solid. 1H NMR (300 MHz, DMSO-d6): δ 2.01 (s, 3H), 3.84 (s, 3H), 3.87 (s, 3H), 8.12 (s, 1H), 10.30 (s, 1H).

Workup

  1. additionwas added
  2. customAfter separating the organic phase
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customDrying under hv

Sources & evidence

ORD record
ord-baf6ae92ca534979af04da8d7131003b
Source dataset
uspto-grants-2013_09
Patent number
US08524899B2

Reaction notes

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