Ethyl Bromide → N-ethyl 4-(4-pyridinyl)isatoic anhydride

HRID 1248465Notes

Reaction equation

HRID 1248465 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]3[NH:15][C:14](=[O:16])[O:13][C:11](=[O:12])[C:10]3=[CH:17][CH:18]=2)=[CH:3][CH:2]=1.[CH2:19](N1C2C(=CC=C(C3C=CC=CN=3)C=2)C(=O)C(C(O)=O)=C1)[CH3:20].C(Br)C>>[CH2:19]([N:15]1[C:14](=[O:16])[O:13][C:11](=[O:12])[C:10]2=[CH:17][CH:18]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH:8]=[C:9]12)[CH3:20]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 103346241-Ethyl-1,4-dihydro-4-oxo-7-(2-pyridinyl)-3-quinolinecarboxylic acidHCID 134704437-(Pyridin-4-yl)-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 10038659N-ethyl 4-(4-pyridinyl)isatoic anhydride

Procedure

It was found that the 4-(4-pyridinyl)isatoic anhydride prepared in the preceding examples could be converted to 1-ethyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acid by (a) alkylating it with ethyl bromide, as in Ranken et al., to produce N-ethyl-4-(4-pyridinyl)isatoic anhydride, (b) reacting the N-ethyl-4-(4-pyridinyl)isatoic anhydride with the potassium salt of ethyl formyl acetate to form ethyl 1-ethyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylate, and (c) hydrolyzing that ester.

Sources & evidence

ORD record
ord-c6ec551346c44c13adae86f7567bc6f0
Source dataset
uspto-grants-1985_06
Patent number
US04524203

Reaction notes

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