Hydrazine hydrate (1:1) → (5-Bromopyridin-2-yl)methanamine

HRID 877784Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:6][CH:7]=1.O.NN>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-((5-bromopyridin-2-yl)methyl)isoindoline-1,3-dione from Step 1 of Example 265 (630 mg, 1.987 mmol) and hydrazine monohydrate (0.484 mL, 9.93 mmol) was heated to 70° C. for 1.5 hr. A thick suspension formed. after cooling to rt, the reaction mixture was diluted with 20 ml of EtOH, filtered and the filter cake was washed with EtOH. The filtrate was concentrated to ⅓ volume and was refiltered. Concentration of that filtrate afforded (5-bromopyridin-2-yl)methanamine (364 mg, 1.946 mmol, 98% yield) as a colorless semisolid. 1H NMR (400 MHz, DMSO-d6) δ 8.58 (d, J=2.2 Hz, 1H), 7.99 (dd, J=8.4, 2.4 Hz, 1H), 7.45 (dd, J=8.4, 0.4 Hz, 1H), 3.77 (s, 2H). MS (ES+) m/z: 187.12, 189.07 (M+H); LC retention time: 0.298 min (analytical HPLC Method O).

Workup

customA thick suspension formed
temperatureafter cooling to rt
filtrationfiltered
washthe filter cake was washed with EtOH
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-181afac131dc4bf4921013f2cfc031b9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987268B2

Reaction notes

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