Hydrazine hydrate (1:1) → HCID 22890458, compound

HRID 896744Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([NH:30][C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)[CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)=[C:11]([N+:39]([O-:41])=[O:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:19][CH2:18][CH:17]([NH:30][C:31]1[CH:32]=[CH:33][C:34]([C:35]#[N:36])=[CH:37][CH:38]=1)[C:12]1[CH:13]=[C:14]([O:15][CH3:16])[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[N+:39]([O-:41])=[O:40]

Participants

Conditions

Temperature: 60 °C

Procedure

4-[1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-benzonitrile (2.7 g, 5 mmoles) was dissolved in ethanol (100 ml) and hydrazine hydrate (0.65 ml, 20 mmoles) added. The reaction was heated to 60° C. for 3 hours then at room temperature for 48 hours. The solids that precipitated were filtered off and the residue submitted to flash chromatography to yield 4-[2-Amino-1-(4-benzyloxy-5-methoxy-2-nitro-phenyl)-ethylamino]-benzonitrile (1.5 g). 1HNMR(CDCl3): 7.75 (s,1H), 7.3-7.5 (m, 7H), 7.05 (s,1H), 6.45 (d, 2H), 5.80 (bs, 1H), 5.32 (m, 1H), 5.19 (s, 2H), 3.81 (s, 3H), 3.25 (dd, 1H), 3.0 (dd, 1H), 1.65 (bs, 2H).

Workup

customThe solids that precipitated
filtrationwere filtered off

Sources & evidence

ORD record: ord-ed4c9103fef94a7183a8c6ef079fe5df
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919369B2

Reaction notes

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