Triethylamine → HCID 53808791, compound

HRID 1646219Notes

Reaction equation

HRID 1646219 reaction equation
[C:1]1(=[O:15])[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([N:18]([CH2:21]C)[CH2:19]C)C>COC(OC)N(C)C>[CH3:16][N:18]([CH:21]=[C:2]1[CH2:3][CH2:4][C:5]2[C:14](=[CH:13][C:12]3[C:7]([N:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:1]1=[O:15])[CH3:19]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10081421HCID 10081421, compound

Product 1

HCID 53808791HCID 53808791, compound

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

3,4-Dihydroacridin-1(2H)-one (19.43 g) was refluxed in N,N-dimethylformamide dimethyl acetal (48.57 ml) and triethylamine (13.76 ml) for 10 hours. The reaction was concentrated and thereafter, triturated first with diethyl ether/pentane and then with diethyl ether, to yield 22.43 g of 2-(dimethylaminomethylene)-3,4-dihydroacridin-1(2H)-one. This was combined with an additional 1.07 g of compound and refluxed in hydrazine (12.68 ml) and ethanol (372 ml) for 2.5 hours. The reaction was cooled, concentrated, and triturated with diethyl ether to yield 20.67 g of a pale orange crystalline solid. A 3.5 g portion was recrystallized from methanol and dried under high vacuum and refluxing xylenes for 30 hours to yield 1.60 g of an off-white crystalline solid, mp 248°-248.5° C.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated first with diethyl ether/pentane

Sources & evidence

ORD record
ord-3615ef6517a1412a8bb55657f769f3a4
Source dataset
uspto-grants-1993_01
Patent number
US05179100

Reaction notes

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