Diisopropylethylamine → HCID 18353658, compound

HRID 430073Notes

Reaction equation

HRID 430073 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:14][CH2:15][CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].C(N(C(C)C)CC)(C)C>>[CH2:19]([O:18][CH:17]([O:21][CH2:22][CH3:23])[CH2:16][CH2:15][NH:14][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:20]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 123691662-Chloro-4-methoxyquinoline

Product 1

HCID 18353658HCID 18353658, compoundYield 12%

Conditions

Temperature
95 °C

Procedure

To 2-chloro-4-methoxyquinoline (0.576 g, 3 mmol) was added 1-amino-3,3-diethoxypropane (0.515 g, 3.5 mmol) and diisopropylethylamine (5 ml). The mixture was stirred under argon at 95° C. for 60 h. Volatile material was removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate soluble material was purified by chromatography on silica gel eluting with 0-10% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a yellow gum (110 mg, 12%). δH (CD3OD) 1.1 (6H, t), 1.85 (2H, m), 3.35-3.7 (6H, m), 3.9 (3H, s), 4.6(1H, t), 6.05(1H, s), 7.0(1H, t), 7.35 (1H, t), 7.45 (1H, d), 7.8 (1H, d); MS (ES+) 305 (63%, MH+). 259 (28), 213 (42), 187 (100).

Workup

  1. customVolatile material was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe ethyl acetate soluble material was purified by chromatography on silica gel eluting with 0-10% (9:1 MeOH/NH3) in dichloromethane

Sources & evidence

ORD record
ord-fcb17d0f57c94b68a1f51147d729c3f6
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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