Nicotinoyl chloride → HCID 67297989, compound

HRID 1520305Notes

Reaction equation

HRID 1520305 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>C1COCC1.CCN(CC)CC>[C:4]([C:3]1[CH:7]=[C:8]([O:11][CH2:12][CH2:13][CH3:14])[CH:9]=[CH:10][C:2]=1[NH:1][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1)(=[O:5])[NH2:6]

Participants

5

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 61307255HCID 61307255, compound

Product 1

HCID 67297989HCID 67297989, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-amino-5-propoxy-benzamide (760 mg, 3.91 mmol) in THF (15 mL) and Et3N (1 mL) was added nicotinoyl chloride (607 mg, 4.30 mmol) in anhydrous THF (15 min) dropwise. The resulting mixture was stirred at room temperature for 3 h. After the reaction was completed, the volatiles were removed. The residue was washed with H2O (10 mL). The pH was adjusted to approximately 5 by adding dilute HCl (2N in water). The resulting solid was collected and dried in vacuo to give 1.00 g of iii-a as a pale yellow solid (89.0%). LCMS m/z=300.1 (M+1) (Method B) (retention time=1.60 min).

Workup

  1. customthe volatiles were removed
  2. washThe residue was washed with H2O (10 mL)
  3. additionby adding dilute HCl (2N in water)
  4. customThe resulting solid was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-01776709e1c74db2be4ca86773879368
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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