Methyl 2-chloro-10-nitromethyl-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylate → Methyl 10-aminomethyl-2-chloro-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylate

HRID 2040937Notes

Reaction equation

HRID 2040937 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH:9]([CH2:15][N+:16]([O-])=O)[CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[CH:3]=1.[H][H]>O1CCCC1.[Ni]>[NH2:16][CH2:15][CH:9]1[C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[O:6][C:5]2[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][C:4]=2[CH:10]1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 66860014Methyl 2-chloro-10-nitromethyl-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58160337Methyl 10-aminomethyl-2-chloro-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous slurry of Ni-Raney (containing 30 g of Ni on a dry basis) was washed with tetrahydrofuran, and added over a solution of 270 g (0.78 mol) of methyl 2-chloro-10-nitromethyl-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylate (compound XIa), as obtained in Example 18, in 2.7 L of tetrahydrofuran. The suspension was stirred under 50-60 psi (3447-4136 hPa) of hydrogen at room temperature for 2 days. The catalyst was removed by filtration, and the resulting solution was concentrated under reduced pressure to obtain methyl 10-aminomethyl-2-chloro-10,11-dihydrodibenzo[b,f]oxepine-11-carboxylate (compound XIIa), which was used in the next step (see Example 20) without further purification.

Workup

  1. washwas washed with tetrahydrofuran
  2. customThe catalyst was removed by filtration
  3. concentrationthe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4b287166018c4c1e80e8b9de4d0cce9a
Source dataset
uspto-grants-2013_11
Patent number
US08580972B2

Reaction notes

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