Hydrazine hydrate (1:1) → HCID 67263815, compound

HRID 1687054Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:18]([N+:19]([O-])=O)=[CH:17][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:11][C:5]=2[CH:4]=1.O.NN>CO.[Pd]>[CH3:1][O:2][C:3]1[C:18]([NH2:19])=[CH:17][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]([F:14])([F:15])[F:16])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a 1-neck round-bottom flask was added 7-methoxy-8-nitro-3-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (310 mg, 1.0 mmol), hydrazine monohydrate (10 mL, 0.2 mol), palladium (10% wt on C, 50% wet; 100 mg, 0.9 mmol), in methanol (20 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite and was concentrated. The resulting precipitate was partitioned between water and dichloromethane. The organic phase was washed with another portion of water, dried (MgSO4), and concentrated, to afford 8-methoxy-3-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (245 mg, 88%) as a waxy solid, which was used without further purification. m.p. ° C.; 1H-NMR (CDCl3) δ 6.55 (s, 1H), 6.49 (s, 1H), 3.82 (s, 3H), 3.63 (br s, 2H), 3.15 (q, J=9.5 hz, 2H), 2.88 (m, 4H), 2.77 (m, 4H); LC/MS (ESI+): 275.07 (M+H).

Workup

filtrationThe reaction mixture was filtered through Celite
concentrationwas concentrated
customThe resulting precipitate was partitioned between water and dichloromethane
washThe organic phase was washed with another portion of water
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-b3197ebffc8843048504522d2aaf23e8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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