Formic Acid → HCID 22712342, compound

HRID 394575Notes

Reaction equation

HRID 394575 reaction equation
C=O.C(O)=O.[Br:6][C:7]1[CH:13]=[CH:12][C:10](N)=[C:9](C)[C:8]=1[N+:15]([O-:17])=[O:16].[CH3:18][N:19]([CH:21]=O)[CH3:20]>>[CH3:18][N:19]([CH3:20])[C:21]1[CH:12]=[CH:13][C:7]([Br:6])=[C:8]([N+:15]([O-:17])=[O:16])[C:9]=1[CH3:10]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 6228Dimethylformamide2×HCID 227123394-Bromo-2-methyl-3-nitroaniline

Product 1

HCID 22712342HCID 22712342, compound

Procedure

5.8 g of paraformaldehyde and 15 ml of formic acid are dissolved in 15 ml of DMF and heated to 90° C.-100° C. A solution of 18 g of 4-bromo-2-methyl-3-nitroaniline in 15 ml of DMF is added dropwise within 10 minutes. After 2 hours, the mixture is added to about 600 ml of ice water and the aqueous phase is extracted with 300 ml of ether. The organic phase is washed with Na2CO3 (1M), filtered and evaporated down. The product is purified by chromatography (silica gel, eluant: petroleum ether/ethyl acetate (40/60). 15 g of N,N-dimethyl-4-bromo-2-methyl-3-nitroaniline is obtained as a brownish-orange oil.

Workup

  1. temperatureheated to 90° C.-100° C
  2. extractionthe aqueous phase is extracted with 300 ml of ether
  3. washThe organic phase is washed with Na2CO3 (1M)
  4. filtrationfiltered
  5. customevaporated down
  6. customThe product is purified by chromatography (silica gel, eluant

Sources & evidence

ORD record
ord-41cae8c194804849a1a2181d90428e73
Source dataset
uspto-grants-2003_08
Patent number
US06602897B2

Reaction notes

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