Nitric Acid → HCID 14209957, compound

HRID 1031440Notes

Reaction equation

HRID 1031440 reaction equation
[N+]([O-])(O)=O.[C:5]([NH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[N+:24]([O-])=O)[NH:20][C:19](=[O:27])[CH2:18][CH2:17]2)(=O)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1>>[N:9]1[CH:10]=[CH:11][C:6]([C:5]2[NH:13][C:14]3=[CH:15][C:16]4[CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]=4[CH:22]=[C:23]3[N:24]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 14209951HCID 14209951, compound

Product 1

HCID 14209957HCID 14209957, compound

Conditions

Temperature
25 °C

Procedure

22.7 g. (85 mmole) of the above amide were slowly introduced at 5° C. into 120 ml. 65% nitric acid. The reaction mixture was further stirred at 25° C. for 1 hour, poured on to ice and filtered off with suction. The residue was purified over silica gel (elution agent: methylene chloride/methanol saturated with ammonia; 95:5 v/v) to give 2.4 g. (10% of theory) 6-isonicotinoylamino-7-nitro-1,2,3,4-tetrahydroquinolin-2-one; m.p. 285 -288° C.

Workup

  1. additionpoured on to ice
  2. filtrationfiltered off with suction
  3. customThe residue was purified over silica gel (elution agent: methylene chloride/methanol saturated with ammonia; 95:5 v/v)
  4. customto give 2.4 g

Sources & evidence

ORD record
ord-ad763a1cfe66441e9c5f1e97b2e8542d
Source dataset
uspto-grants-1990_09
Patent number
US04954498

Reaction notes

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