Tert-Butylamine → HCID 21450279, compound

HRID 1579280Notes

Reaction equation

HRID 1579280 reaction equation
[O:1]1[CH2:21][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23]>CO>[C:22]([NH:26][CH2:21][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 21450271HCID 21450271, compound

Product 1

HCID 21450279HCID 21450279, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of crude 6-[4-(2,3-epoxypropoxy)-3-nitrophenyl]-4,5-dihydro-3(2H)-pyridazinone (3.3 g, 0.011 mole), methanol (70 ml), and t-butylamine (7.2 ml, 0.068 mole), was gently heated under reflux for 105 minutes. The filtered solution was evaporated under reduced pressure to an orange coloured foam (4 g, 97%). The crude base (3.77 g) was digested with water (200 ml) and glacial acetic acid added to pH 4, then the solution filtered and washed with dichloromethane (3 × 100 ml). The aqueous phase was treated with potassium carbonate solution to pH 9, then extracted with dichloromethane and the combined organic extracts washed with a little water. Evaporation of the dried solution gave crude 6-[4-(3-t-butylamino-2-hydroxypropoxy)-3-nitrophenyl]-4,5-dihydro-3(2H)-pyridazinone (2.82 g, m.p. about 92°-105°C). After two recrystallisations from ethyl acetate the free base (m.p. about 124°C) was converted into its hydrochloride m.p. 260°-262°C. The pure hydrochloride recrystallised from methanol-ether, had m.p. 263°-265°C (decomposition).

Workup

  1. temperaturewas gently heated
  2. temperatureunder reflux for 105 minutes
  3. customThe filtered solution was evaporated under reduced pressure to an orange coloured foam (4 g, 97%)
  4. additionadded to pH 4
  5. filtrationthe solution filtered
  6. washwashed with dichloromethane (3 × 100 ml)
  7. additionThe aqueous phase was treated with potassium carbonate solution to pH 9
  8. extractionextracted with dichloromethane
  9. washthe combined organic extracts washed with a little water
  10. customEvaporation of the dried solution

Sources & evidence

ORD record
ord-6fba8dafd9b341ff8c271b7ddde55023
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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