Pyridine → HCID 59129384, compound

HRID 1991734Notes

Reaction equation

HRID 1991734 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[C:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15].N1C=CC=CC=1.[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[C:26]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[C:12][C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])(=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 59129298Methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate

Product 1

HCID 59129384HCID 59129384, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (260 mg, 1.0 mmol) and pyridine (160 mg, 2.0 mol) in CH2Cl2 (20 mL) was added butyryl chloride (140 mg, 1.3 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 3 h before the mixture was poured into ice-water. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain methyl 4-(2-butyramido-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (150 mg, 45%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ 8.79 (brs, 1H), 8.71 (d, J=9.2 Hz, 1H), 8.24 (d, J=2.8 Hz, 1H), 8.17 (dd, J=2.8, 9.2 Hz, 1H), 3.82 (s, 3H), 2.55 (t, J=7.2 Hz, 2H), 1.85-1.75 (m, 2H), 1.63 (s, 6H), 1.06 (t, J=6.8 Hz, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (30 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6c705a8b5c94116b4c6cd7e1a854723
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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