4-Tert-Butylaniline → HCID 11304276, compound

HRID 2054152Notes

Reaction equation

HRID 2054152 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[C:19]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>O1CCOCC1>[ClH:1].[C:19]([C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]4[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=4)=[CH:9][CH:10]=3)[CH:5]=[N:4][N:3]=2)=[CH:28][CH:29]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 86009609HCID 86009609, compound

Product 1

HCID 11304276HCID 11304276, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Chloro-6-(3-methyl-2-pyridinyl)phthalazine (200 mg; 0.78 mmol) and 4-tert-butylaniline (117 mg, 0.125 mL; 0.78 mmol) in 1,4-dioxane were heated at reflux for 2 h. After allowing to cool down to room temperature the precipitate was collected by filtration washed with 1,4-dioxane and dried to give the title compound (135 mg) (43%). 1H NMR (500 MHz, DMSO-d6) δ: 1.35 (9H, s), 7.48 (1H, dd, J 4.9 and 7.6 Hz), 7.55-7.61 (4H, m), 7.90 (1H, dd, J 0.8 and 7.8 Hz), 8.47 (1H, dd, J 1.6 and 8.6 Hz), 8.52 (1H, d, J 2.0 Hz), 8.63 (1H, dd, J 1.2 and 4.7 Hz), 9.09 (1H, d, J 8.6), 9.32 (1H, s); MS (ES M+1) 369.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationwas collected by filtration
  3. washwashed with 1,4-dioxane
  4. customdried

Sources & evidence

ORD record
ord-f4a8b4b0d7964491ac30c418aa311958
Source dataset
uspto-grants-2008_02
Patent number
US07329659B2

Reaction notes

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