Acrylic Acid → 4(1H)-Quinolinone, 8-amino-2,3-dihydro-

HRID 1886443Notes

Reaction equation

HRID 1886443 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][C:13]([OH:15])=O)([O-])=O.ClC1C=CC(NCCC(O)=O)=C([N+]([O-])=O)C=1.ClC1C([N+]([O-])=O)=C(NCCC(O)=O)C=CC=1.C(O)(=O)C=C.[N+](C1C=CC=C2C=1NCCC2=O)([O-])=O.ClC1C([N+]([O-])=O)=C2C(C(=O)CCN2)=CC=1.FC1C=C2C(=C([N+]([O-])=O)C=1)NCCC2=O.CC1C([N+]([O-])=O)=C2C(C(=O)CCN2)=CC=1.[Sn](Cl)(Cl)(Cl)Cl.Cl.Cl.[Sn]>Cl.[Fe].C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[NH:10][CH2:11][CH2:12][C:13]2=[O:15]

Participants

13

Reactant 10

HCID 6581Acrylic AcidHCID 3047333-(4-Chloro-2-nitroanilino)propanoic acidHCID 30902033-[(2-Nitrophenyl)amino]propanoic acidHCID 107279787-chloro-2,3-dihydro-8-nitro-4(1H)-quinolinoneHCID 122973628-Nitro-2,3-dihydroquinolin-4(1H)-one2×HCID 185486766-fluoro-2,3-dihydro-8-nitro-4(1H)-quinolinoneHCID 198759993-(3-Chloro-2-nitrophenylamino)propionic acidHCID 198760092,3-dihydro-7-methyl-8-nitro-4(1H)-quinolinoneHCID 86739978Tin hydrochlorideHCID 86746162Tin chloride hydrochloric acid

Product 1

HCID 122973664(1H)-Quinolinone, 8-amino-2,3-dihydro-

Reagents, catalysts & solvents 2

HCID 45051903EisenazetatCatalystHCID 86633186Hydrochloric acid-ironCatalyst

Procedure

By Friedel-Crafts reaction, known compounds 3-(2nitrophenylamino)propionic acid, 3-(4-chloro-2-nitrophenylamino)propionic acid, 3-(3-chloro-2-nitrophenylamino)propionic acid [Ann. Chim. (Rome), volume 55, page 182 (1965)] or substituted N-(2-carboxyethyl)-2-nitroanilin compounds, which can generally be prepared by reacting known substituted 2-nitroaniline with acrylic acid, are converted into novel 2,3-dihydro-8-nitro-4(1H)-quinolinone compounds such as 7-chloro-2,3-dihydro-8-nitro-4(1H)-quinolinone, 6-fluoro-2,3-dihydro-8-nitro-4(1H)-quinolinone and 2,3-dihydro-7-methyl-8-nitro-4(1H)-quinolinone. The 2,3-dihydro-8-nitro-4(1H)-quinolinone compounds are reduced by tin chloride - hydrochloric acid, tin - hydrochloric acid, iron - hydrochloric acid, iron - acetic acid or by catalytic hydrogenation to give 8-amino-2,3-dihydro-4(1H)-quinolinone compounds represented by the formula (IV): ##STR4## wherein R2, R3 and R4 have the same significances as defined above.

Workup

  1. customBy Friedel-Crafts reaction
  2. customcan generally be prepared

Sources & evidence

ORD record
ord-272a0f32744f437d9d5833e18851c1aa
Source dataset
uspto-grants-1992_09
Patent number
US05151431

Reaction notes

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