Dimethylformamide → HCID 13958331, compound

HRID 2090251Notes

Reaction equation

HRID 2090251 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1O)=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-:7])=[O:6].CN(C=O)C.[NH2:24][CH2:25][CH2:26][CH2:27][OH:28]>C(Cl)Cl>[N+:5]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 90863-Amino-1-propanolHCID 24386Thionyl ChlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 13958331HCID 13958331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (6.3 mL) was added to a mixture of 3-nitroquinolin-4-ol (15 g) and DMF (6.9 mL) in DCM (200 mL). The mixture was heated under reflux for 3 h then cooled to 0° C. 3-Amino-1-propanol (7.3 mL) was added slowly followed by dropwise addition of TEA (36 mL) and the mixture stirred at rt for 3 h. The precipitate was filtered, washed with DCM then water. The DCM filtrate was washed with water and evaporated under reduced pressure then combined with the filtered solid. The combined solids were triturated with ether and filtered to give a yellow solid, 19.2 g

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationThe precipitate was filtered
  4. washwashed with DCM
  5. washThe DCM filtrate was washed with water
  6. customevaporated under reduced pressure
  7. customThe combined solids were triturated with ether
  8. filtrationfiltered
  9. customto give a yellow solid, 19.2 g

Sources & evidence

ORD record
ord-f69c7726fac44047bafee6e218cbf243
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

Loading…