1-Methylimidazole → 863886-03-7

HRID 1907891Notes

Reaction equation

HRID 1907891 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][CH3:12])[CH:3]=1.[Li+].[Cl-].CCN(C(C)C)C(C)C.[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:27])[CH:25]=[CH2:26].CN1C=CN=C1>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][NH:11][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH:26]=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27]

Participants

8

Reactant 5

HCID 13901-MethylimidazoleHCID 8846Butyl AcrylateHCID 81531DiisopropylethylamineHCID 2580415-chloro-N-methyl-2-nitroanilineHCID 433294Lithium Chloride

Product 1

HCID 66835685863886-03-7

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 4-chloro-2-methylaminonitrobenzene (50.0 g, 268.0 mmol, 1.0 eq), Pd(OAc)2 (0.30 g, 1.3 mmol, 0.005 eq) and LiCl (11.4 g 268.0 mmol, 1.0 eq) in DMAc (250 mL) was added iPr2NEt (56 mL, 321.5 mmol, 1.2 eq) followed by n-butyl acrylate (40 mL, 281.4 mmol, 1.05 eq) under nitrogen. The reaction mixture was stirred at 110° C. for 12 h, then cooled to 50° C. 1-methylimidazole (10.6 mL, 134.0 mmol, 0.5 eq) was added and the mixture was stirred for 30 min before filtering and adding water (250 mL). The resulting mixture was cooled to r.t. over 1 h. The resulting solid was filtered and washed with water and dried to yield n-butyl 3-methylamino-4-nitrocinnamate (71.8 g, 96%, 99.2 A % purity).

Workup

  1. temperaturecooled to 50° C
  2. stirringthe mixture was stirred for 30 min
  3. filtrationbefore filtering
  4. additionadding water (250 mL)
  5. temperatureThe resulting mixture was cooled to r.t. over 1 h
  6. filtrationThe resulting solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d425e3b5424740d19c088e94c7ec6394
Source dataset
uspto-grants-2013_12
Patent number
US08598183B2

Reaction notes

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