Anthranilic Acid → HCID 19773186, compound

HRID 1614200Notes

Reaction equation

HRID 1614200 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2CCC(NC1C=CC=CC=1C(O)=O)=O.CC1(C)OC(=O)[CH:30]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[C:40](OC)[CH:41]=3)[NH:36][C:35]=2C)C(=O)O1.[C:48]([OH:57])(=O)[C:49]1[C:50](=[CH:52][CH:53]=[CH:54][CH:55]=1)[NH2:51]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:30][CH2:34][C:35]1[N:36]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:48](=[O:57])[C:49]3[C:50](=[CH:52][CH:53]=[CH:54][CH:55]=3)[N:51]=1)=[CH:6]2

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 15675566HCID 15675566, compoundHCID 67794349HCID 67794349, compound

Product 1

HCID 19773186HCID 19773186, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The foregoing intermediate product 3-(5-methoxyindol-3-yl)-N-(2-carboxyphenyl)propionamide can be prepared directly from the corresponding Meldrum's Adduct [3-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)-methyl-5-methoxyindole] (4.41 g, 14.5 mmol) by reaction with an equivalent amount of anthranilic acid (1.99 g, 14.5 mmol) in 30 ml of pyridine. The reaction is carried out at reflux for two hours after which the pyridine is azeotropically removed under vacuum with toluene [Route B].

Workup

  1. customis azeotropically removed under vacuum with toluene [Route B]

Sources & evidence

ORD record
ord-cc253e9d418940a785bc3c5fa8d1f22d
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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