Hydrochloric Acid → HCID 178520397, compound

HRID 1447287Notes

Reaction equation

HRID 1447287 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=2)[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1)=[O:5])#[N:2].C(N(CC)CC)C.[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+].Cl>CO.CN(C)C=O>[NH:30]1[C:1]([CH2:3][C:4]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[NH:14][C:15](=[O:22])[C:16](=[CH:20][CH:21]=3)[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=2)=[O:5])=[N:2][N:32]=[N:31]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 128378436-[4-(Cyanoacetylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid

Product 1

HCID 178520397HCID 178520397, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.4 g (45 mmol) of 6-(4-cyanoacetylaminophenyl)-1,2-dihydro-2-oxonicotinic acid from Example 5, 130 ml of dimethylformamide, 6.3 ml (45 mmol) of triethylamine, 9.75 g (150 mol) of sodium azide, and 8.03 g (150 mmol) of ammonium chloride is heated on the steam bath for 48 hrs. The reaction mixture is diluted with 600 ml of methanol and the resulting solution slowly acidified with 90 ml of 2 N hydrochloric acid. The precipitated solid is filtered, washed with methanol, and dried under vacuum at 60° for 24 hours to give 12.3 g of 6-[4-[(1H-tetrazol-5-ylacetyl)amino]phenyl]-1,2-dihydro-2-oxonicotinic acid.

Workup

  1. temperatureis heated on the steam bath for 48 hrs
  2. filtrationThe precipitated solid is filtered
  3. washwashed with methanol
  4. customdried under vacuum at 60° for 24 hours

Sources & evidence

ORD record
ord-1dca3c1b252347a8a6d2833fc3430533
Source dataset
uspto-grants-1982_02
Patent number
US04315858

Reaction notes

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