Acetic Acid → Ethyl 1-(4-fluorophenyl)-6-(morpholinomethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1048876Notes

Reaction equation

HRID 1048876 reaction equation
BrC1C=C2C(=CC=1)N(C1C=CC(F)=CC=1)C=C(C(OCC)=O)C2=O.[F:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:41]3[C:36](=[CH:37][C:38]([CH:42]=[O:43])=[CH:39][CH:40]=3)[C:35](=[O:44])[C:34]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:33]2)=[CH:28][CH:27]=1.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[C:41]3[C:36](=[CH:37][C:38]([CH:42]=[O:43])=[CH:39][CH:40]=3)[C:35](=[O:44])[C:34]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:33]2)=[CH:30][CH:31]=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([N:32]2[C:41]3[C:36](=[CH:37][C:38]([CH2:42][N:50]4[CH2:55][CH2:54][O:53][CH2:52][CH2:51]4)=[CH:39][CH:40]=3)[C:35](=[O:44])[C:34]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:33]2)=[CH:30][CH:31]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 121447931Ethyl 1-(4-fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 121447944Ethyl 6-bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 2

HCID 121447931Ethyl 1-(4-fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 121458875Ethyl 1-(4-fluorophenyl)-6-(morpholinomethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 194.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 1-(4-fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (H) was prepared from compound D via a method analogous to that described in Example 3. After stirring for two hours, a solution of compound H (10 mg, 0.030 mmol), morpholine (3.1 μL, 0.035 mmol), and acetic acid (4.2 μL, 0.074 mmol) in dichloromethane (1 mL) was treated with sodium triacetoxyborohydride (9.4 mg, 0.044 mmol). After stirring 16 hours, the reaction was concentrated to dryness to give 12 mg (99%) of the title compound that was used without further purification. ES-MS [M+1]+: 411.3.

Workup

  1. stirringAfter stirring 16 hours
  2. concentrationthe reaction was concentrated to dryness

Sources & evidence

ORD record
ord-07199b158d264047a3ee85086f78d49a
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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