Ammonia → HCID 13113742, compound

HRID 1421456Notes

Reaction equation

HRID 1421456 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=[O:13].C(O)(C)(C)C.N.[Li].[Cl-].[NH4+].Cl>O1CCCC1>[O:2]=[C:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH:4]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

8

Reactant 6

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 25517Ammonium ChlorideHCID 744692,5-Dimethoxyphenylacetic acidHCID 3028194Lithium

Product 1

HCID 13113742HCID 13113742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.6 g (20 mmol) of (2,5-dimethoxyphenyl) acetic acid, 30 g (0.4 mole) of anhydrous t-butanol, and 40 ml of anhydrous tetrahydrofuran (THF) was added to 200 ml of liquid ammonia at -78° C. via cannula. Lithium wire (1.5 g, 0.21 mol) was cut into small pieces, washed briefly with isopropylalcohol and hexane, and then added to the above mixture piece by piece. The resulting reaction mixture turned a dark blue-gray color. After 4 hours, the blue color faded to gray, some excess ammonium chloride (4 g) was added, and the ammonia was allowed to evaporate overnight under a stream of nitrogen, leaving a white solid. The residue was then treated with 80 ml of 6 N hydrochloric acid, and the resultant mixture was heated to reflux for 1.5 hours.

Workup

  1. washwashed briefly with isopropylalcohol and hexane
  2. additionadded to the above mixture piece by piece
  3. customThe resulting reaction mixture
  4. additionwas added
  5. customto evaporate overnight under a stream of nitrogen
  6. customleaving a white solid
  7. temperatureto reflux for 1.5 hours

Sources & evidence

ORD record
ord-061cca7d349f4dbe90942ba07c0b7238
Source dataset
uspto-grants-2000_06
Patent number
US06077653

Reaction notes

Loading…