Hydrazine hydrate (1:1) → 5-(Biphenyl-3-yl)pent-4-yn-1-amine

HRID 473519Notes

Reaction equation

[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH:2]=1.O.NN>C(O)C>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(5-(Biphenyl-3-yl)pent-4-ynyl)isoindoline-1,3-dione (0.11 g, 0.30 mmol) and hydrazine monohydrate (0.030 mL, 0.60 mmol) were taken up into ethanol (3 mL) and stirred at 80° C. for 2.5 hours. The resulting mixture was filtered and the solvent removed in vacuo to yield 5-(biphenyl-3-yl)pent-4-yn-1-amine, which was used in the next step without further purification. MH+ 236.2

Workup

filtrationThe resulting mixture was filtered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-2b29983d2073463bb3f6c54ebd36bc76
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633322B2

Reaction notes

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