Triethylamine → 1-(4-Methoxy-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

HRID 227089Notes

Reaction equation

HRID 227089 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[C:10]([C:19]([OH:21])=O)=[CH:9]2)=[CH:5][CH:4]=1.Cl.[CH3:25][NH:26][O:27][CH3:28].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(#N)C>[CH3:28][O:27][N:26]([CH3:25])[C:19]([C:10]1[C:11](=[O:18])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]([CH2:7][C:6]2[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:9]=1)=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 111923Propylphosphonic anhydrideHCID 14767561-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 577547631-(4-Methoxy-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Experimental conditions analogous to those described for Step 5 of Example 60, from crude 1-(4-Methoxy-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 1.03 g (10.6 mmol) of N,O-dimethylhydroxylamine hydrochloride, 6.1 mL (4.43 g, 43.8 mmol) of triethylamine and 6.3 mL (6.80 g, 10.7 mmol) of 50% 1-propanephosphonic acid cyclic anhydride in 30 mL acetonitrile to give 1.90 g of the product as an off-white solid.

Sources & evidence

ORD record
ord-d2a98fe4435c44f3a8a99b57f2f8a73e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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