Acetic Anhydride → HCID 15593372, compound

HRID 1733220Notes

Reaction equation

HRID 1733220 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([OH:18])=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([O:3][CH3:4])=[O:2].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]([O:18][C:19](=[O:21])[CH3:20])=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15573072HCID 15573072, compound

Product 1

HCID 15593372HCID 15593372, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Four grams of 1-carbomethoxy-4-hydroxy-9H-pyrido[3,4-b]-indole were dissolved in a mixture of 20 ml pyridine and 24 ml acetic anhydride and the solution was allowed to stand at room temperature overnight. The resultant crystals were collected by filtration and recrystallized from methanol to yield 2.9 g of the title compound. Yield 61.8% colorless prisms, m.p. 220°-221° C. Elemental analysis--found: C, 63.23%; H, 3.94%, N, 9.59%; calculated for C15H12N2O4 (mol. wt. 284): C, 63.38%; H, 4.26%; N, 9.86%. Mol. wt. (based on mass spectrum) 284. NMR (DMSO-d6): δ2.62 ppm, 3H (COCH3), 4.07 ppm, 3H (COOCH3), 8.37 ppm, 1H (3-H), 7.20-8.20 ppm, 4H, 11.85 ppm; 1H (NH). UV spectrum (methanol): 360, 300, 264, 243, 212 mμ. IR spectrum: 3380, 1760, 1675, 1242, 1222 cm-1.

Workup

  1. filtrationThe resultant crystals were collected by filtration
  2. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e9095322439a4121a0fe94551a691980
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

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