Anthranilic Acid → HCID 19773186, compound

HRID 1461358Notes

Reaction equation

HRID 1461358 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-d1bda7bd94f34e3cb7dd0ffb36577bc5
Source dataset
uspto-grants-1991_12
Patent number
US05075313

Reaction notes

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