1-Methylimidazole → HCID 89814428, compound

HRID 715085Notes

Reaction equation

HRID 715085 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15](OC(=O)CC)(=O)[CH2:16]C.CN1C=CN=C1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH2:15][CH3:16])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 31263Propionic anhydrideHCID 111272614-Fluoro-3-nitrophenylacetic acid

Product 1

HCID 89814428HCID 89814428, compoundYield 52.2%

Procedure

Treat a solution of 2-(4-fluoro-3-nitrophenyl)acetic acid (1.5 g, 7.53 mmol) in propionic anhydride (5.40 mL, 45.2 mmol) with 1-methylimidazole (0.600 mL, 7.53 mmol) and stir at RT overnight. Quench the mixture with H2O, stir for 1 h, extract with EtOAc (2×), wash the combined organics with satd. Na2CO3, then brine, dry the organics over MgSO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (830 mg, 52%). 1H NMR (400 MHz, DMSO-d6): δ 8.00 (dd, J=7.4, 2.2 Hz, 1H), 7.61 (ddd, J=8.6, 4.6, 2.2 Hz, 1H), 7.53 (dd, J=11.4, 8.6 Hz, 1H), 3.95 (s, 2H), 2.56 (q, J=7.3 Hz, 2H), 0.96 (t, J=7.3 Hz, 3H); MS (ESI) m/z: 212.1 (M+H+).

Workup

  1. customQuench the mixture with H2O
  2. stirringstir for 1 h
  3. extractionextract with EtOAc (2×)
  4. washwash the combined organics with satd
  5. dry with materialNa2CO3, then brine, dry the organics over MgSO4
  6. concentrationconcentrate to dryness
  7. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-bfc68fa92f2f4a08b78cafe03444fc8c
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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