Ammonia → HCID 86761171, compound

HRID 1712219Notes

Reaction equation

HRID 1712219 reaction equation
[Na].N.[CH3:3][C:4]1[CH:5]=[C:6]([P:11]([C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)C2C=C(C)C=C(C)C=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1.[C:28]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35](Cl)[N:34]=1)([CH3:31])([CH3:30])[CH3:29]>O1CCCC1>[C:28]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35]([P:11]([C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)[C:6]2[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH3:3])[CH:5]=2)[N:34]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 112263Phosphine, tris(3,5-dimethylphenyl)-HCID 5360545SodiumHCID 221415801-t-Butoxy-3-chloroisoquinoline

Product 1

HCID 86761171HCID 86761171, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., sodium (0.28 g, 12.3 mmol) is added slowly to liquid ammonia (40 mL) followed by tris(3,5-dimethylphenyl)phosphine (2.1 g, 6.0 mmol), and the resulting mixture is stirred for 2 hours. A solution of 1-tert-butoxy-3-chloroisoquinoline (1.4 g, 6.0 mmol) in tetrahydrofuran (6 mL) is then added drop-wise and the resulting mixture slowly warmed to ambient temperature over 16 hours. The residue is quenched with water (30 mL), extracted with diethyl ether (3×25 mL), and the combined extracts are percolated through a column of magnesium sulfate-ZSM-5. The filtrate is concentrated under reduced pressure and the opaque residue is purified by a re-crystallization from methanol, yielding 1-tert-butoxy-3-(bis(3,5-dimethylphenyl)phosphino)isoquinoline (0.94 g, 73%) as a white solid.

Workup

  1. customThe residue is quenched with water (30 mL)
  2. extractionextracted with diethyl ether (3×25 mL)
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe opaque residue is purified by a re-crystallization from methanol

Sources & evidence

ORD record
ord-ab063ed0b5754896a03036a3ae8ee6c9
Source dataset
uspto-grants-2010_09
Patent number
US07790932B1

Reaction notes

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