Water → HCID 58438090, compound

HRID 2092381Notes

Reaction equation

HRID 2092381 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7483N-Methyl-4-nitroanilineHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 58438090HCID 58438090, compoundYield 126.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methyl-4-nitroaniline (5 g, 32.9 mmol) in DMF (75 ml) was slowly added NaH (60% in mineral oil, 4.21 g, 105 mmol) at RT (Warning: important gaz evolution occurred!). The suspension was vigorously stirred at RT for 15 min then cooled to 0° C. (ice bath). 4-(Chloromethyl)pyridine hydrochloride (8.09 g, 49.3 mmol) was added carefully then the slurry was allowed to warm to RT and further stirred for 45 min. The reaction mixture was poured into water and extracted with Et2O (3×). The combined organic phases were dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (10.13 g) as an orange solid, which was used in the next step without further purification. HPLC: AtRet=1.01 min; LC-MS: m/z 244.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.23 (s, 3H), 4.82 (s, 2H), 6.77-6.83 (m, 2H), 7.17-7.22 (m, 2H), 8.02-8.08 (m, 2H), 8.49-8.54 (m, 2H).

Workup

  1. customat RT
  2. temperaturethen cooled to 0° C. (ice bath)
  3. temperatureto warm to RT
  4. stirringfurther stirred for 45 min
  5. extractionextracted with Et2O (3×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-e2cdca2edad740d7b4e129d1122fd5f7
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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