Ethanol hydrochloride → HCID 136051886, compound

HRID 369545Notes

Reaction equation

HRID 369545 reaction equation
C[C@H](OC1C(N)=CC(O)=C([N+]([O-])=O)C=1)CCCCCC.N([O-])=O.[Na+].Cl.C(O)C.[CH3:29][C@H:30]([O:37][C:38]1[C:43]([N:44]=[N:45][C:46]2[CH:51]=[C:50]([O:52][C@@H:53](C)[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:49]([N:61]([CH3:63])[CH3:62])=[CH:48][C:47]=2[OH:64])=[CH:42][C:41]([OH:65])=[C:40]([N+:66]([O-:68])=[O:67])[CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>N1C=CC=CC=1>[CH3:29][C@H:30]([O:37][C:38]1[C:43]([N:44]=[N:45][C:46]2[CH:51]=[C:50]([O:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:49]([N:61]([CH3:62])[CH3:63])=[CH:48][C:47]=2[OH:64])=[CH:42][C:41]([OH:65])=[C:40]([N+:66]([O-:68])=[O:67])[CH:39]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 21887872Ethanol hydrochlorideHCID 23668193Sodium NitriteHCID 54565707HCID 54565707, compoundHCID 135971980HCID 135971980, compound

Product 1

HCID 136051886HCID 136051886, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 43b (143 mg, 0.57 mmol), compound 51a (161 mg, 0.57 mmol), 0.1 M aqueous sodium nitrite (5.6 ml), and pyridine (1.8 ml) in 15 ml of a 15% HCl/ethanol solution were reacted according to the procedure for compound 52a. The crude product was adsorbed onto silica gel and purified via flash chromatography with gradual elutions from 85/10/5 to 75/20/5 (Hex/EtOAc/dichloromethane). Evaporation of solvent yielded 199 mg (64%) of a metallic green solid.

Workup

  1. custompurified via flash chromatography with gradual elutions from 85/10/5 to 75/20/5 (Hex/EtOAc/dichloromethane)
  2. customEvaporation of solvent

Sources & evidence

ORD record
ord-dde2cedd77084a6a808383f03a7fd4ef
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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