1-Chloroethyl chloroformate → HCID 14822508, compound

HRID 2073788Notes

Reaction equation

HRID 2073788 reaction equation
[Br:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=3)[N:4]([CH2:17][CH2:18][N:19](C)[CH3:20])[N:3]=1.ClC(OC(Cl)C)=O>C(Cl)Cl>[Br:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=3)[N:4]([CH2:17][CH2:18][NH:19][CH3:20])[N:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 14822504HCID 14822504, compound

Product 1

HCID 14822508HCID 14822508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-7-methoxy-1-(2-methylaminoethyl)-1H-pyrazolo[3,4-b]quinoline was prepared by demethylation of 3-bromo-1-[2-(dimethylamino)ethyl]-7-methoxy-1H-pyrazolo[3,4-b]quinoline (Example 37) by the method of J. Org. Chem. 49, 2081 (1984), as follows: to a mixture of 15 g of the compound of Example 37 and 150 ml methylene dichloride at 0° C. was added dropwise a solution of 6.7 g α-chloroethyl chloroformate in 30 ml methylene dichloride. The reaction mixture was heated at reflux for one hour and then concentrated to remove solvent. The residue in 300 ml methanol was heated at reflux for one hour. The methanol was removed, ice-water and concentrated ammonium hydroxide added to the residue, and the product collected and recrystallized from ethyl acetate to give 7.12 g 3-bromo-7-methoxy-1-(2-methylaminoethyl)-1H-pyrazolo[3,4-b]quinoline, light yellow powder, m.p. 100°-101° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. concentrationconcentrated
  4. customto remove solvent
  5. temperatureThe residue in 300 ml methanol was heated
  6. temperatureat reflux for one hour
  7. customThe methanol was removed
  8. additionice-water and concentrated ammonium hydroxide added to the residue
  9. customthe product collected
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ca3d043c2c74bb6bbf70409ce5bb4ac
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

Loading…