2-Methyl-6-nitroaniline → HCID 10609959, compound

HRID 1378739Notes

Reaction equation

HRID 1378739 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:4].Br[C:13](C)(C)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(C(C)C)CC)(C)C>>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][NH:4][C:3]1[C:2]([CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[N+:9]([O-:11])=[O:10])[CH3:18]

Participants

4

Reactant 3

HCID 112982-Methyl-6-nitroanilineHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 10609959HCID 10609959, compound

Procedure

A mixture of 2-methyl-6-nitroaniline (XIV, 2.00 g), ethyl bromoacetate (III, 3.5 ml) and diisopropylethylamine (3.5 ml) is heated at reflux (140°) for 8 hr. The resultant solution is allowed to cool to 20°-25°. After dilution with aqueous sodium bicarbonate, extraction several times with ethyl acetate, drying with magnesium sulfate and concentration the residue is resubmitted to the above reaction conditions for an additional 16 hr. After workup, purification by flash chromatography eluting with a gradient of hexane/ethyl acetate (10/1→5/1), pooling and concentrating the appropriate fractions, the title compound is obtained, mp 49°-52°; IR (mineral oil) 3365, 2953, 2925, 1731, 1536, 1475, 1461, 1374, 1344, 1236, 1207, 1104 and 1022 cm-1 ; NMR (CDCl3) 7.88, 7.33, 6.8-7.0, 6.86, 4.17, 3.94, 2.39 and 1.23 δ.

Workup

  1. temperatureis heated
  2. temperatureat reflux (140°) for 8 hr
  3. temperatureto cool to 20°-25°
  4. extractionAfter dilution with aqueous sodium bicarbonate, extraction several times with ethyl acetate
  5. dry with materialdrying with magnesium sulfate and concentration the residue
  6. customis resubmitted to the above reaction conditions for an additional 16 hr
  7. customAfter workup, purification by flash chromatography
  8. washeluting with a gradient of hexane/ethyl acetate (10/1→5/1)
  9. concentrationconcentrating the appropriate fractions

Sources & evidence

ORD record
ord-ecd08d1f4ab541fb8e2f870602839bb8
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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