4-Isopropylaniline → HCID 18671717, compound

HRID 1384127Notes

Reaction equation

HRID 1384127 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[ClH:15].C(N(CC)CC)C.[CH:23]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)([CH3:25])[CH3:24].[N:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:43](=O)[NH:42][N:41]=2)=[CH:35][CH:34]=1>O>[ClH:15].[ClH:15].[CH:23]([C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:43]2[C:44]3[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:40]([CH2:39][C:36]3[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=3)=[N:41][N:42]=2)=[CH:28][CH:27]=1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 74644-IsopropylanilineHCID 11130Triethylamine hydrochlorideHCID 14812Phosphorus oxide (P4O10)HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

Product 1

HCID 18671717HCID 18671717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

In the manner described in Example 45, a mixture of 1.80 g (12.68 mmol) phosphorus pentoxide, 1.73 g (12.6 mmol) triethylamine hydrochloride, 1.8 ml (12.74 mmol) 4-isopropylaniline, and 1 g (4.2 mmol) 4-(4-pyridylmethyl)-1 (2H)-phthalazinone is stirred for 4 h at 210° C. The frozen melt is then suspended in water using an ultrasonic bath, filtered, and the filtrate evaporated in the RE. The oil-like residue is distributed between dichloromethane and a mixture of 20 ml water and 5 ml conc. ammonia, and the organic phase dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The residue is then stirred with acetonitrile, filtered off from some non-transformed 4-(4-pyridylmethyl)-1 (2H)-phthalazinone, and the filtrate evaporated under vacuum. Flash chromatography of the residue on silica gel with a particle size of 0.04-0.06 mm using acetate/methanol mixtures (20:1 and 10:1) yields a resin (free base of the title compound), which is dissolved in a mixture of 4 ml methanol and 1.5 ml of 3N methanolic HCl. After evaporation under vacuum, recrystallization of the residue from methanol/ether, drying under HV (8 h, 120° C.), and equilibration for 16 h at 20° C. and in room atmosphere, title compound is obtained with a water content of 9.4%; m.p. >250° C.; ESI-MS: (M+H)+=355.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in the RE
  3. additiona mixture of 20 ml water and 5 ml conc. ammonia
  4. dry with materialthe organic phase dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. stirringThe residue is then stirred with acetonitrile
  8. filtrationfiltered off from some non-transformed 4-(4-pyridylmethyl)-1 (2H)-phthalazinone
  9. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-1f6be3d43ffa4fc9a52277e8fe125ee8
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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