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

HRID 227081Notes

Reaction equation

HRID 227081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8]([C:17](O)=[O:18])=[CH:7]1.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(#N)C>[CH3:27][O:26][N:25]([CH3:24])[C:17]([C:8]1[C:9](=[O:16])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]([CH2:5][C:4]2[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=2)[CH:7]=1)=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 111923Propylphosphonic anhydrideHCID 567718851-(3-Chlorobenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 577546151-(3-Chloro-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-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 2.21 g (22.6 mmol) of N,O-dimethylhydroxylamine hydrochloride, 14.3 mL (10.4 g, 103 mmol) of triethylamine and 14.6 mL (15.6 g, 24.5 mmol) of 50% 1-propanephosphonic acid cyclic anhydride in 100 mL acetonitrile to give 3.10 g of the product as an off-white solid.

Sources & evidence

ORD record
ord-d82f04629f184132a3091aac713343b3
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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