Anthranilic Acid → HCID 13730771, compound

HRID 1650093Notes

Reaction equation

HRID 1650093 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Br[C:12]1[C:13](=[O:25])[N:14]([C:18]([CH:22]([CH3:24])[CH3:23])([CH3:21])[C:19]#[N:20])[C:15](=[O:17])[CH:16]=1.C(O)(C)C.C([O-])(=O)C.[Na+]>CCOCC>[C:19]([C:18]([N:14]1[C:13](=[O:25])[CH:12]=[C:16]([NH:4][C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([OH:10])=[O:9])[C:15]1=[O:17])([CH3:21])[CH:22]([CH3:23])[CH3:24])#[N:20]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 3776IsopropanolHCID 517045Sodium AcetateHCID 19352213HCID 19352213, compound

Product 1

HCID 13730771HCID 13730771, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of anthranilic acid, (13.7 g, 0.1 mol), 3-bromo-α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (27 g, 0.1 mol), isopropanol (200 ml) and sodium acetate (8.2 g) is stirred at room temperature 3 days and then is heated at reflux 1 hour. On cooling, and with the addition of ether, a yellow solid 31.6 g, (97.7%) is obtained, mp 262°-266° C. after crystallizing from acetic acid. Anal. calcd. for C17H17N3O4 : C, 62.37; H, 5.24; N, 12.84. Found: C, 62.24; H, 5.19; N, 12.70.

Workup

  1. temperatureis heated
  2. temperatureat reflux 1 hour
  3. temperatureOn cooling

Sources & evidence

ORD record
ord-79e6908ccfce4d3aaed4cd55d536ced1
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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