Water → HCID 22163774, compound

HRID 1087738Notes

Reaction equation

HRID 1087738 reaction equation
F[B-](F)(F)F.NC1O[C:9]([CH:20]([CH3:22])[CH3:21])=[N+:10]2[N:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=12.[C:23]1([C:29]#[C:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN1CCN(C)C1=O>[CH:20]([C:9]1[N:10]2[N:19]=[CH:18][C:17]3[C:12]([C:11]2=[C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:13][CH:14]=[CH:15][CH:16]=3)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 22163777HCID 22163777, compound

Product 1

HCID 22163774HCID 22163774, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-amino-3-isopropyloxazolo[4,3-a]phthalazinium tetrafluoroborate (1.58 g) and ethyl phenylpropiolate (1.74 g) in 1,3-dimethyl-imidazolin-2-one (30 ml) was maintained at 40° C. for 19 hours and then the resulting brown solution was poured into water (200 ml), and the mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml). The extracts were combined, dried over magnesium sulphate, and evaporated, and the resulting residue was subjected to flash chromatography on silica gel, using as eluant a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v), to give ethyl 3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine-2-carboxylate (0.72 g) in the form of a yellow solid, m.p. 141°-142° C. [Elemental analysis: C, 77.1; H, 6.24; N, 7.8%; calculated C, 77.1; H, 6.19; N, 7.8%; NMR (in CDCl3) : 0.93 (3H, t, J=7 Hz), 1.57 (6H, d, J=7 Hz), 4.08 (2H, q, J=7 Hz), 4.35 (1H, septet, J=7 Hz), 7.23-7.50 (8H, m), 7.60-7.66 (1H, m), 8.35 (1H, s); Mass spectrum (electron impact) m/z=358].

Workup

  1. extractionthe mixture was extracted with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (1:1 v/v; 3×200 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. additiona mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (19:1 v/v)

Sources & evidence

ORD record
ord-1bc7dd6db92f418ca6bef08ae3eeacfb
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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