Hydrochloric Acid → HCID 19087767, compound

HRID 1464375Notes

Reaction equation

HRID 1464375 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl.N([O-])=O.[Na+].[N:24]#[N:25]>O.C(O)C>[N:1]([C:2]1[CH:3]=[C:4]([CH:9]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8])=[N+:24]=[N-:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 19087766HCID 19087766, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19087767HCID 19087767, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

5.0 g (20 mmol) of the crude product from Example XII are dissolved in 20 ml of H2O, 10 ml of ethanol and 20 ml of conc. HCl and the solution is diazotised at 0° C. with 1.8 g (26 mmol) of sodium nitrite in 10 ml of H2O. After evolution of N2 has ended, the mixture is extracted three times with 100 ml of CH2Cl2, the organic phases are concentrated and the residue is chromatographed on silica gel 60 (CH2Cl2 /MeOH=100:2).

Workup

  1. extractionthe mixture is extracted three times with 100 ml of CH2Cl2
  2. concentrationthe organic phases are concentrated
  3. customthe residue is chromatographed on silica gel 60 (CH2Cl2 /MeOH=100:2)

Sources & evidence

ORD record
ord-e155e63dc5674beea263e03641a00e9b
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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