Triethylamine → 7,8-Dimethoxypyrimido-[4,5-b]-Quinolin-4(3H)-One-2-Hydroxamic Acid

HRID 1112255Notes

Reaction equation

HRID 1112255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]1[N:15]=[C:16]([C:20](OCC)=[O:21])[NH:17][C:18](=[O:19])[C:7]1=[CH:6]2.Cl.[NH2:26][OH:27].C(N(CC)CC)C>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]1[N:15]=[C:16]([C:20]([NH:26][OH:27])=[O:21])[NH:17][C:18](=[O:19])[C:7]1=[CH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 135445830Pirolate

Product 1

HCID 1357053267,8-Dimethoxypyrimido-[4,5-b]-Quinolin-4(3H)-One-2-Hydroxamic AcidYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Ethyl 7,8-dimethoxypyrimido-[4,5-b]quinolin-4(3H)-one-2-carboxylate (200 mg., 6.08 millimoles) is added to a solution of hydroxylamine hydrochloride (69 mg., 100 millimoles) and triethylamine (100 mg., 100 millimiles) in absolute ethanol (50 ml.). The mixture is heated at 95° C. overnight in a bomb and then cooled. The insoluble yellow solid is filtered off, washed with hot ethanol and dried to provide 143 mg. (74%) of the title product. M.P. 337° C. (dec.).

Workup

  1. temperaturecooled
  2. filtrationThe insoluble yellow solid is filtered off
  3. washwashed with hot ethanol
  4. customdried
  5. customto provide 143 mg

Sources & evidence

ORD record
ord-db967f556dd94c8a8b1b97524d533934
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

Loading…