Diisopropylethylamine → Nitrofungin

HRID 1873703Notes

Reaction equation

HRID 1873703 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([C:12]([O:14][C:15](C)(C)C)=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:32]=1[O:33]C1C2C(=CC(OC)=C(C(OC)=O)C=2)N=CC=1>CN1CCCC1=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:30][C:31]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:32]=1[OH:33]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 66916250HCID 66916250, compoundHCID 866506961,1-Dimethylethyl 4-chloro-7-methoxy-6-quinolinecarboxylate

Product 2

HCID 12074NitrofunginHCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Similar to the synthesis of compound 1a, from methyl 4-chloro-7-methoxyquinoline-6-carboxylate (350 mg), 2-chloro-4-nitrophenol (240 mg), N,N-diisopropylethylamine (484 μL), and N-methylpyrrolidin-2-one (1.5 mL), compound 48a was yielded (130 mg, yield: 24%).

Sources & evidence

ORD record
ord-545b2dec3c154e9089fa44eb01e10721
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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