2-Naphthalenesulfonyl chloride → HCID 23002656, compound

HRID 398330Notes

Reaction equation

HRID 398330 reaction equation
[CH:1]1([CH2:11][C:12]([OH:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[OH-].[Na+].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>O1CCOCC1.O>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]1[CH2:11][C:12]([OH:14])=[O:13])(=[O:28])=[O:29]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 2733683(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid

Product 1

HCID 23002656HCID 23002656, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.91 g of (1,2,3,4-tetrahydro-1-isoquinolyl)-acetic acid (Preparation 2.18) are suspended in 25 ml of dioxane, 10 ml of 1N NaOH are added, followed by portionwise addition of 2.3 g of 2-naphthalenesulphonyl chloride, and the mixture is maintained at pH=10.5-12 by addition of 1N NaOH. The mixture is kept stirring at a constant pH for 2 hours at RT. The reaction medium is diluted with 100 ml of water and is then washed twice with EtOAc and brought to pH=1.2 by addition of 6N HCl in the presence of EtOAc. This mixture is extracted with EtOAc, washed with saturated NaCl solution, dried over Na2SO4 and evaporated to dryness. The expected product crystallizes from heptane, and is drained, washed with heptane and then dried to give 3.14 g, m.p.=132° C.

Workup

  1. washis then washed twice with EtOAc
  2. additionbrought to pH=1.2 by addition of 6N HCl in the presence of EtOAc
  3. extractionThis mixture is extracted with EtOAc
  4. washwashed with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe expected product crystallizes from heptane
  8. washwashed with heptane
  9. customdried
  10. customto give 3.14 g, m.p.=132° C.

Sources & evidence

ORD record
ord-57cfa01a8ff444f289eeeff2e5df4108
Source dataset
uspto-grants-2003_08
Patent number
US06610882B2

Reaction notes

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