Aniline → HCID 59743111, compound

HRID 1667411Notes

Reaction equation

HRID 1667411 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].C([BH3-])#N.[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 5003444Sodium cyanoborohydrideHCID 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 cyanoborohydride (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-7aa444f08f2e4a66b2bc4a070c23d393
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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