Phosgene → 7-(Pyridin-4-yl)-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 1583644Notes

Reaction equation

HRID 1583644 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.C(N1C2C(=CC=C(C3C=CC=CN=3)C=2)[C:24](=[O:37])C(C(O)=O)=C1)C.NC1C=C(C2C=CN=CC=2)C=CC=1C(O)=O.C(Cl)(Cl)=O>>[N:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:12]=[C:4]3[NH:1][C:24](=[O:37])[O:8][C:6](=[O:7])[C:5]3=[CH:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 103346241-Ethyl-1,4-dihydro-4-oxo-7-(2-pyridinyl)-3-quinolinecarboxylic acidHCID 134892172-Amino-4-(pyridin-4-yl)benzoic acid2×HCID 134919902-Nitro-4-(pyridin-4-yl)benzoic acid

Product 1

HCID 134704437-(Pyridin-4-yl)-2H-3,1-benzoxazine-2,4(1H)-dione

Procedure

It was found that the 2-nitro-4-(4-pyridinyl)benzoic acid prepared in the preceding examples could be converted to 1-ethyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acid by (a) reducing it to 2-amino-4-(4-pyridinyl)benzoic acid, (b) reacting the 2-amino-4-(4-pyridinyl)benzoic acid with phosgene to form 4-(4-pyridinyl)isatoic anhydride, (c) alkylating the 4-(4-pyridinyl)isatoic anhydride with ethyl bromide to produce N-ethyl-4-(4-pyridinyl)isatoic anhydride, (d) 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 (e) hydrolyzing that ester.

Sources & evidence

ORD record
ord-3895bdf10cb54c5e90a032554e5d3dd2
Source dataset
uspto-grants-1985_11
Patent number
US04552966

Reaction notes

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