Acetyl chloride → HCID 16779266, compound

HRID 1958522Notes

Reaction equation

HRID 1958522 reaction equation
[ClH:1].[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=[O:13])[NH:3]1.[OH-].[Na+].[C:17](Cl)(=[O:19])[CH3:18]>CC(C)=O>[Cl:1][C:5]1[CH:6]=[CH:7][C:18]([C:17]([N:3]2[CH:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2]2)=[O:19])=[CH:12][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium Hydroxide2×HCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Product 1

HCID 16779266HCID 16779266, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride (10.00 g, 46.8 mmol) was added portionwise into a mixture of acetone (75 mL) and 2N NaOH (75 mL). To this solution was added dropwise acetyl chloride (8.75 mL, 50 mmol) in acetone (50 mL) followed with 2N NaOH at room temperature. The reaction mixture was maintained at a pH>10 and stirred for 1 hour. The acetone was removed by evaporation under reduced pressure and acidified the residue by adding 3N HCl. The separated solid was collected by filtration, washed several times with water, and dried to give 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid as an enantiomeric mixture, 13.80 g (93.4%); mp 77-79° C.; 1H NMR (DMSO-d6) δ 2.92 (1H, dd, J=5.9 Hz and J=15.8 Hz, CH), 3.29 (1H, d, J=15.8 Hz, CH), 4.12 (1H, d, J=5.9 Hz, CH), 4.49 and 5.02 (each 1H, d, J=17.4 Hz, CH2), 7.09-7.17 (4H, m, 4×ArH), 7.40-7.58 (4H, m, 4×ArH); m/z 315.00 (M+H)+ Anal. Calcld. for C17H14ClNO3: C, 64.67; H, 4.47; N, 4.44. Found: C, 64.65; H, 4.46; N, 4.41.

Workup

  1. temperatureThe reaction mixture was maintained at a pH>10
  2. customThe acetone was removed by evaporation under reduced pressure
  3. additionby adding 3N HCl
  4. filtrationThe separated solid was collected by filtration
  5. washwashed several times with water
  6. customdried

Sources & evidence

ORD record
ord-8a9b8838f42d4f6e85f5c711059a6feb
Source dataset
uspto-grants-2013_04
Patent number
US08410130B2

Reaction notes

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