Pyridine → HCID 59129428, compound

HRID 1847744Notes

Reaction equation

HRID 1847744 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([F:14])[C:6]=1[NH2:15].N1C=CC=CC=1.[C:24](Cl)(=[O:28])[CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([F:14])[C:6]=1[NH:15][C:24](=[O:28])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 591292912-(3,3-Dimethyl-but-1-ynyl)-6-fluoro-4-nitro-phenylamine

Product 1

HCID 59129428HCID 59129428, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3,3-dimethyl-but-1-ynyl)-6-fluoro-4-nitro-phenylamine (4.0 g, 17 mmol) and pyridine (2.7 g, 34 mmol) in anhydrous CH2Cl2 (30 mL) was added and butyryl chloride (1.8 g, 17 mmol) dropwise at 0° C. After stirring for 5 h at 0° C., the reaction mixture was poured into ice (50 g) and extracted with CH2Cl2 (30 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give N-[2-(3,3-dimethyl-but-1-ynyl)-6-fluoro-4-nitro-phenyl]-butyramide (3.2 g, 62%), which was used in the next step without further purification. 1H NMR (300 MHz, DMSO) δ 8.10 (dd, J=1.5, 2.7 Hz, 1H), 7.95 (dd, J=2.4, 9.6 Hz, 1H), 7.22 (brs, 1H), 2.45 (t, J=7.5 Hz, 2H), 1.82 (m, 2H), 1.36 (s, 9H), 1.06 (t, J=7.5 Hz, 3H).

Workup

  1. customdropwise at 0° C
  2. extractionextracted with CH2Cl2 (30 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-49e2be30b408405a8f9e844ac9dcb9d6
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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