Diethyl Ether → (4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methanamine

HRID 627115Notes

Reaction equation

HRID 627115 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][C:6]([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([CH2:25][N:26]3C(=O)C4C(=CC=CC=4)C3=O)[CH:10]=2)=[CH:5][CH:4]=1.O.NN.CCOCC.C1(=O)C2C(=CC=CC=2)C(=O)NN1>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([CH2:25][NH2:26])[CH:10]=2)=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)2×HCID 2194012,3-Dihydro-1,4-phthalazinedioneHCID 898519332-((4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione2×

Product 1

HCID 89851364(4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of 2-((4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione (Intermediate 64, 1.1 g, 2.15 mmol) in chloroform (20 mL) and methanol (10 mL) at room temperature was added hydrazine hydrate (0.328 mL, 4.31 mmol). The reaction was stirred overnight at room temperature. Another 1 eq of hydrazine hydrate was added. After 4 hours the reaction mixture was filtered to remove the solids. The filtrate was concentrated to afford an orange oil. The oil was dissolved in methanol and ether was added to crash out more solids. This was repeated until no 2,3-dihydrophthalazine-1,4-dione by product remained. The title compound was obtained as an orange foam (0.82 g, 100%).

Workup

  1. filtrationAfter 4 hours the reaction mixture was filtered
  2. customto remove the solids
  3. concentrationThe filtrate was concentrated
  4. customto afford an orange oil

Sources & evidence

ORD record
ord-6f7ee73ab7754f2886be353d658b8a81
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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