Ammonium Chloride → HCID 58036795, compound

HRID 1952006Notes

Reaction equation

HRID 1952006 reaction equation
[Li][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:8]1([P:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH4+].[Cl-]>C1COCC1>[C:25]1([P:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[NH:23][CH:22]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:21]=[CH:20]3)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 628659Quinoline, 8-(diphenylphosphino)-HCID 178506676HCID 178506676, compound

Product 1

HCID 58036795HCID 58036795, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

PhLi (0.56 mL, 1.8M in di-n-butyl ether, 1 mmol) was added to a stirred solution of 8-diphenylphoshinoquinoline (1) (156 mg, 0.5 mmol) in dry THF (5 mL) at −78° C. and the solution was stirred at 0° C. for 10 minutes. The solution was then cooled to −78° C., saturated aqueous NH4Cl solution (10 mL) was added and the mixture was warmed to room temperature. Products were extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give 4 (196 mg) quantitatively as a yellow oil. 1H NMR (400.13 MHz, CDCl3) δ 7.4-7.3 (m, 15H, Ph-H), 6.92 (d, 1H, J=7.2 Hz, C5—H), 6.69 (ddd, 1H, J=7.2, 6.0, 1.2 Hz, C7—H), 6.54 (t, 1H, J=7.2 Hz, C6—H), 6.38 (d, 1H, J=9.6 Hz, C4—H), 5.64 (dd, 1H, J=10.0, 4.0 Hz, C3—H), 5.44 (bs, 1H, N1—H), 5.15 (d, 1H, J=7.2 Hz, C2—H) ppm; 13C NMR (100.61 MHz, CDCl3) δ 146.5 (d, J=19.2 Hz), 145.1, 135.4 (d, J=8.1 Hz), 135.3 (d, J=7.1 Hz), 134.5, 133.7 (d, J=18.2 Hz), 133.6 (d, J=19.2 Hz), 133.4 (d, J=19.2 Hz), 127.3, 128.7-128.3 (m), 127.1, 126.0, 125.2, 124.5, 119.1, 117.1, 116.1 (d, J=8.1 Hz), 57.6 ppm; 31P NMR (161.97 MHz, CDCl3) δ −23.8 ppm.

Workup

  1. temperatureThe solution was then cooled to −78° C.
  2. temperaturethe mixture was warmed to room temperature
  3. extractionProducts were extracted with EtOAc
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-68727307705b4579b8e3408b77b03a09
Source dataset
uspto-grants-2013_03
Patent number
US08404843B2

Reaction notes

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