Hydrazine hydrate (1:1) → [(4-(Allyloxylmethyl)phenyl)(phenyl)methylene]hydrazine

HRID 40453Notes

Reaction equation

HRID 40453 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[CH:8][CH:7]=1)[CH:2]=[CH2:3].O.[NH2:21][NH2:22]>CO>[CH2:1]([O:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([C:10](=[N:21][NH2:22])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 212535414-(Allyloxymethyl)benzophenone

Product 1

HCID 72240815[(4-(Allyloxylmethyl)phenyl)(phenyl)methylene]hydrazineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of 9 (1.09 g, 43 mmol) in methanol (10 ml) was added hydrazine hydrate (1.08 g 20 mmol). The mixture was heated to reflux for 48 h. then concentrated in vacuo. The residue was partioned between DCM and water and the organic layer collected and concentrated to yield 10 (1.10 g, 98%) as a mixture of cis and trans isomers and as a yellow oil; δH (CDCl3) 4.03, 4.13 (2×dt, 2H, J=1.4, 5.6 Hz, OCH2CH═CH2) 4.52, 4.60 (2×s, 2H, ArCH2O), 5.20, 5.27 (ddd, 1H, J=1.4, 3.0, 10.4 Hz, OCH2CH═CHH), 5.32, 5.37 (ddd, 1H, J=1.4, 3.2, 17.3 Hz, OCH2CH═CHH), 5.45 (bs, 2H, NNH2), 5.91-6.06 (m, 1H, OCH2CH═CH2), 7.28-7.31 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.46-7.55 (m, 5H, 2-, 2′-, 4′-, 6-, 6′-H) ppm; δC (CDCl3) 60.1, 71.5, 71.7 (ArCH2O, OCH2CH═CH2), 117.0, 117.3 (OCH2CH═CH2), 126.3, 126.4, 127.4, 128.0, 128.5, 128.7, 129.3 (Ar—C), 134.4, 134.6 (2×OCH2CH═CH2), 137.7, 138.1, 139.1 (Ar—C), 148.7 (C═N) ppm; νmax (thin film) 3404, 3289, 3057, 2855, 1612, 1444, 1411, 1277, 1083 cm−1; m/z (ES+) 267 ([M+H]+, 100%); found (EST+) 267.1492, C17H19N2O requires 267.1492.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 h.
  3. concentrationthen concentrated in vacuo
  4. customthe organic layer collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eebd226f0cb94e6d925a29d25902f4b2
Source dataset
uspto-grants-2013_09
Patent number
US08530212B2

Reaction notes

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