Isoamyl Nitrite → HCID 178499160, compound

HRID 223590Notes

Reaction equation

HRID 223590 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[S:4][C:3]=1[C:12](=[O:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(O[N:25]=O)CC(C)C>C(O)(=O)C.O1CCOCC1>[C:14]([C:13]1[N:25]=[N:1][C:2]2[C:10]3[CH:9]=[CH:8][C:7]([CH3:11])=[N:6][C:5]=3[S:4][C:3]=2[C:12]=1[OH:18])([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 8053Isoamyl NitriteHCID 20521592HCID 20521592, compound

Product 1

HCID 178499160HCID 178499160, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6 g (0.022 mol) of 3-amino-2-carbomethoxyacetyl-6-methyl-thieno[2,3-b]pyridine in 1.8 ml acetic acid and 180 ml dioxane was slowly added 4.8 g (4.2 ml, 0.041 mol) of isoamylnitrite and stirring continued for 24 hours. It was then poured on ice-water, filtered and washed with water. The crude product was crystallized from DMSO/H2O to give 4.0 g (64%) of 3-carbomethoxy-4-hydroxy-7-methylpyrido[3',2':4,5]-thieno[3,2-c]pyridazine; m.p., 265°-268° C.

Workup

  1. additionIt was then poured on ice-water
  2. filtrationfiltered
  3. washwashed with water
  4. customThe crude product was crystallized from DMSO/H2O

Sources & evidence

ORD record
ord-3f90b45127514ec2b8f6707b29913185
Source dataset
uspto-grants-1982_10
Patent number
US04355164

Reaction notes

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