Hydrazine hydrate (1:1) → HCID 18351448, compound

HRID 430894Notes

Reaction equation

HRID 430894 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[C:18]#[N:19].NN.O>C(O)C>[NH2:3][CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[C:18]#[N:19]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12049511HCID 12049511, compound

Product 1

HCID 18351448HCID 18351448, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-3-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)propenyl]-4-(2-methoxy-ethoxymethoxy)benzonitrile (3.1 g, 8.0 mmol) and NH2NH2 hydrate (0.96 mL, 20 mmol) in ethanol (100 mL) is refluxed for 1.5 hours. The mixture is concentrated, treated with aqueous NaOH, and extracted with CH2Cl2 (3×). The CH2Cl2 layer is dried and concentrated to obtain the product as a clear oil (1.9 g, 7.2 mmol). 1H NMR (CDCl3, 300 MHz) δ7.70 (d, 1H), 7.47 (dd, 1H), 7.22 (d, 1H), 6.75 (d, 1H), 6.34 (m, 1H), 5.35 (s, 2H), 3.80 (t, 2H), 3.50 (m, 4H), 3.27 (s, 3H).

Workup

  1. concentrationThe mixture is concentrated
  2. additiontreated with aqueous NaOH
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe CH2Cl2 layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e96ba03e4ad4d82b40f5781613862b0
Source dataset
uspto-grants-2001_11
Patent number
US06323227B1

Reaction notes

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