Hydrazine hydrate (1:1) → HCID 22890457, compound

HRID 896738Notes

Reaction equation

HRID 896738 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([NH:28][C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:11][C:10]=1[O:37][CH3:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:17][CH2:16][CH:15]([NH:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1)[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([O:37][CH3:38])[CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22890452HCID 22890452, compound

Product 1

HCID 22890457HCID 22890457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

4-[1-(4-Benzyloxy-3-methoxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-benzonitrile B was then dissolved in ethanol (60 ml) and hydrazine hydrate (2 g) was added. The solution was heated to 60-70 degrees C. for 1.5 hours. TLC showed reaction was complete. The suspension was filtered to remove by-product and the ethanol removed in vacuo. The residue was submitted to flash chromatography on silica gel (ethyl acetate: 2N NH3 in methanol, 9:1) to yield 372 mg of 4-[2-Amino-1-(4-benzyloxy-3methoxy-phenyl)-ethylamino]-benzonitrile D (100%). 1HNMR(CDCl3): 7.3-7.45 (m, 7H), 6.32 (m, 3H), 6.5 (d, 2H), 5.52 (d, 1H), 4.3 (q, 1H), 3.83 (s, 3H), 3.08 (m, 2H), 1.95 (s,

Workup

  1. customreaction
  2. filtrationThe suspension was filtered
  3. customto remove by-product
  4. customthe ethanol removed in vacuo

Sources & evidence

ORD record
ord-cc37573b6b004dffa89770a1e50eb31d
Source dataset
uspto-grants-2005_07
Patent number
US06919369B2

Reaction notes

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