Ammonium formate → HCID 18327476, compound

HRID 367007Notes

Reaction equation

HRID 367007 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]([CH3:19])[C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:16][C:14]1[CH:13]=[C:12]([CH3:19])[C:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[C:2]([CH3:1])[CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23287551HCID 23287551, compound

Product 1

HCID 18327476HCID 18327476, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-chloro-9-methoxybenzo[h]-5,6-dihydroquinazoline (50 mg, 0.20 mmol) and 1-[2-(4-amino-2,6-dimethylphenoxy)ethyl]pyrrolidine (47 mg, 0.20 mmol) in ethoxyethanol (2 ml) was treated with hydrogen chloride (0.2 ml of 1.0M HCl in diethyl ether, 0.20 mmol). The resulting mixture was heated at reflux for 6 h, then allowed to cool to room temperature. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic phase dried (MgSO4) and evaporated. The residue was subjected to column chromatography (3-6% methanol-dichloromethane) to afford the title compound as an off-white solid (37 mg) m.p. 123-126°. δH(d6DMSO) 9.28 (1H, s), 8.36 (1H, s), 7.76 (1H, d, J 2.8 Hz), 7.51 (2H, s), 7.26 (1H, d, J 8.3 Hz), 7.01 (1H, dd, J 8.3, 2.8 Hz), 3.85 (3H, s), 3.82 (2H, m), 3.31-2.60 (1H, m), 2.23 (6H, s) and 1.73 (4H, m). 1-[2-(4-amino-2,6-dimethylphenoxy)ethyl]pyrrolidine was prepared by treating a degassed stirring solution of 1-[2-(2,6-dimethyl-4-nitrophenoxy)ethyl]pyrrolidine (824 mg, 3.12 mmol) in ethanol (8 ml) with ammonium formate (590 mg, 9.36 mmol) and 10% palladium on charcoal (100 mg) for 8 h. The mixture was filtered through Celite® and evaporated. The residue was subjected to column chromatography (2-6% methanoldichloromethane) to afford the desired product (489 mg) as a pale yellow oil. 8H (CDCl3) 6.33 (2H, s), 3.84 (2H, t, J 6.3 Hz), 3.38 (2H, br s), 2.90 (2H, t, J 6.3 Hz), 2.65 (4H, m), 2.20 (6H, s) and 1.83 (4H, m). MS (ES+) 235 (MH+)

Workup

  1. additionby treating a degassed
  2. filtrationThe mixture was filtered through Celite®
  3. customevaporated

Sources & evidence

ORD record
ord-83b16e2a80db4bbab414b43697832942
Source dataset
uspto-grants-2000_10
Patent number
US06133257

Reaction notes

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