HCID 22163769, compound → HCID 22163773, compound

HRID 1087740Notes

Reaction equation

HRID 1087740 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[N:7][N:6]2[C:15]=1[CH:16]([CH3:18])[CH3:17]>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH:16]([C:15]1[N:6]2[N:7]=[CH:8][C:9]3[C:14]([C:5]2=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:3]=1[CH:2]=[O:1])=[CH:13][CH:12]=[CH:11][CH:10]=3)([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 22163769HCID 22163769, compound

Product 1

HCID 22163773HCID 22163773, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-hydroxymethyl-3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine (1.22 g) and activated manganese dioxide (18 g) in diethyl ether (200 ml) was stirred at the ambient temperature under an atmosphere of argon for 24 hours. The suspension was then filtered and the solid was extracted with diethyl ether (3×50 ml). The extracts and filtrate were combined and evaporated, and the resulting residue was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (8 ml; 3:1 v/v), to give 3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine-2carboxaldehyde (0.88 g) in the form of a yellow solid, m.p. 163°-164° C. [Elemental analysis: C, 80.4; H, 5.78; N, 8.8%; calculated: C, 80.2; H, 5.77; N, 8.9%; NMR (in CDCl3): 1.52 (6H, d, J=7 Hz), 4.41 (1H, septet, J=7 Hz), 7.30-7.35 (3H, m), 7.42-7.50 (5H, m), 7.58-7.66 (1H, m), 8.34 (1H, s), 9.83 (1H, s); Mass spectrum (electron impact) m/z=314].

Workup

  1. filtrationThe suspension was then filtered
  2. extractionthe solid was extracted with diethyl ether (3×50 ml)
  3. customevaporated
  4. customthe resulting residue was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (8 ml; 3:1 v/v)

Sources & evidence

ORD record
ord-5d170b10d9ae4370aa371bb76b2cc729
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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