HCID 21426389, compound → HCID 178492682, compound

HRID 258671Notes

Reaction equation

HRID 258671 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:10](=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:5]([C:6]([OH:8])=O)[CH:4]=1.[NH2:19][C:20]1[NH:24][N:23]=[N:22][N:21]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[C:15]2[C:10](=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:5]([C:6]([NH:19][C:20]2[NH:24][N:23]=[N:22][N:21]=2)=[O:8])[CH:4]=1

Participants

4

Reactant 2

HCID 21426389HCID 21426389, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178492682HCID 178492682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxy-8-nitroquinaldic acid (3.6 g) (see Example 16) and N,N'-carbonyldiimidazole (2.5 g) in dimethylformamide (70 ml) were heated on a steam bath for 1 hour. 5-Aminotetrazole (2.5 g) was added and the mixture was heated on a steam bath for 1 hour and cooled. 4-Methoxy-8-nitro-N(1H-tetrazol- 5-yl)quinaldamide, compound with imidazole, m.p. 238°, was filtered off and was triturated with 2 N hydrochloric acid (50 ml). 4-Methoxy-8-nitro-N(1H-tetrazol- 5-yl)quinaldamide was collected and dried, m.p. 268° (d).

Workup

  1. temperaturethe mixture was heated on a steam bath for 1 hour
  2. temperaturecooled
  3. filtration4-Methoxy-8-nitro-N(1H-tetrazol- 5-yl)quinaldamide, compound with imidazole, m.p. 238°, was filtered off
  4. customwas triturated with 2 N hydrochloric acid (50 ml)
  5. custom4-Methoxy-8-nitro-N(1H-tetrazol- 5-yl)quinaldamide was collected
  6. customdried

Sources & evidence

ORD record
ord-b384d73b062a4c3ebc00881f940c2df3
Source dataset
uspto-grants-1977_07
Patent number
US04034075

Reaction notes

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