Aniline → HCID 59743111, compound

HRID 1803497Notes

Reaction equation

HRID 1803497 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]=O)=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]S([O-])(=O)=O.[Mg+2].[Na]>C(Cl)Cl.C(O)(=O)C.C1COCC1>[CH3:1][N:2]([CH3:15])[C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5360545SodiumHCID 86620967HCID 86620967, compound

Product 1

HCID 59743111HCID 59743111, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-dimethylamino-phthalazine-6-carbaldehyde (25 mg, 0.13 mmol), aniline (14 μL, 0.15 mmol), THF (1 mL) and MgSO4 (43 mg, 0.357 mmol) were stirred at room temperature. To this mixture was added acetic acid (8 μL) followed by sodium cyanoboroahydride (13 mg, 0.207 mmol) and the reaction stirred for 15 h. The reaction was diluted with CH2Cl2, washed with aq. NaHCO3, dried (Na2SO4) and concentrated. Purification by prep. HPLC yielded the desired compound. m/z 279.22 (M+1).

Workup

  1. stirringthe reaction stirred for 15 h
  2. washwashed with aq. NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by prep

Sources & evidence

ORD record
ord-65f1eab6448d4703b931984b1cffc42b
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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