HCID 67263900, compound → HCID 67263288, compound

HRID 1041492Notes

Reaction equation

HRID 1041492 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]1[NH:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]>[Pd].C(O)C>[NH2:19][C:17]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:2]2[O:3][CH2:4][CH2:5][O:1]2)[CH:18]=1

Participants

4

Reactant 1

HCID 67263900HCID 67263900, compound

Product 1

HCID 67263288HCID 67263288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a par bottle, 2-(2-[1,3]dioxolan-2-yl-imidazolidin-1-yl)-4-nitro-benzonitrile (8.20 g), ethanol (50 mL) and 10% Pd/C (0.50 g) were added. The reaction mixture was evacuated and charged with hydrogen 3 times. The reaction was shaken at room temperature on the par at 45 psi for 4 hours. The solid was filtered and washed with ethanol. The solvent was concentrated to give 4-amino-2-(2-[1,3]dioxolan-2-yl-imidazol-1-yl)-benzonitrile as an off white solid. 1H-NMR (DMSO-D6, 400 MHz): δ 7.52 (d, 1H), 7.40 (s, 1H), 7.03 (s, 1H), 6.68 (d, 1H), 6.60 (s, 1H), 6.45 (bs, 2H), 5.75 (s, 1H), 3.80 (bs, 2H), 3.62 (bs, 2H).

Workup

  1. customThe reaction mixture was evacuated
  2. additioncharged with hydrogen 3 times
  3. filtrationThe solid was filtered
  4. washwashed with ethanol
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-e96c1660d0154dd7b4e34c1ad85d26e7
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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