HCID 178423536, compound → HCID 178423535, compound

HRID 2083206Notes

Reaction equation

HRID 2083206 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([C:18]2[NH:22][N:21]=[N:20][N:19]=2)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:3]2[O:4][C:5]3=[N:13][CH:12]=[CH:11][CH:10]=[C:6]3[C:7](=[O:9])[C:14]=2[CH:15]=[C:16]([C:18]2[NH:19][N:20]=[N:21][N:22]=2)[CH:17]=1

Participants

3

Reactant 1

HCID 178423536HCID 178423536, compound

Product 1

HCID 178423535HCID 178423535, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1 g of 2-[2-methyl-4-(5-1H-tetrazolyl)phenoxy]nicotinic acid and 10 ml of concentrated sulfuric acid is heated at 180° C for 2.5 hours, and then poured into ice water. The crystalline precipitate is filtered off, washed with water and with methanol and recrystallized from dimethylformamide to give 0.5 g of 9-methyl-7-(5-1H-tetrazolyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine melting at 290° C to 291° C with decomposition.

Workup

  1. filtrationThe crystalline precipitate is filtered off
  2. washwashed with water and with methanol
  3. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e1644da96ee449a189cd8ea59ca7e2ae
Source dataset
uspto-grants-1978_04
Patent number
US04085111

Reaction notes

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