Sodium Hydroxide → HCID 53872605, compound

HRID 610640Notes

Reaction equation

[H+].[CH3:2][C@H:3]([NH2:12])[C@H:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[OH-].[Na+].[I:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21]>CCOCC>[I:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH:12][CH:3]([CH3:2])[CH:4]([OH:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a ice-cooled mixture of norephedrine hydrochloride (1) (7.02 g, 37.5 mmol) in Et2O (165 mL) and 55 NaOH aqueous solution (60 mL) was added dropwise a solution of 3-Iodobenzoyl chloride (2b, 10 g, 37.5 mmol) in Et2O (100 mL). After the addition had completed, the resulting mixture was stirred at 0° C. for 4 h. The solvent was removed in vacuo. The residue was washed with H2O, dried, the recrystallized from EtOH to provide a white solid (12.84 g, 90%). mp 139-140.5° C. 1H NMR (CDCl3) d 1.10 (d, J=) 6.9 Hz, 3 H, CH3), 3.51 (d, J=3.3 Hz, 1 H, --CHCH3), 4.42-4.52 (m, 1 H, --OH), 4.97 (bs, 1 H, --CHOH), 6.42 (d, J=7.8 Hz, 1 H, NH), 7.14 (t, J=7.8 Hz, 1 H, aromatic), 7.25-7.42 (m, 5 H, aromatic), 7.69 (d, J=7.8 Hz, 1 H, aromatic), 7.82 (d, J=8.1 Hz, 1 H, aromatic), 8.08 (s, 1 H, aromatic). 13C NMR (CDCl3) d 14.20 (q, CH3), 51.45 (d, --CHCH3), 76.18 (d, --CHOH), 94.24 (s, =CI--, aromatic), 126.14 (d, 2C, aromatic), 127.63 (d, aromatic), 128.26 (d, aromatic), 130.19 (d, aromatic), 136.00 (d, aromatic), 136.25 (s, aromatic), 140.41 (d, aromatic), 140.55 (s, aromatic), 166.26 (s, aromatic). Anal. Calcd. for C16H16INO2 : C, 50.41; H, 4.23; N, 3.67. Found: C, 50.48; H, 4.28; N, 3.62.

Workup

additionAfter the addition
customThe solvent was removed in vacuo
washThe residue was washed with H2O
customdried
customthe recrystallized from EtOH

Sources & evidence

ORD record: ord-cf6b50874a7f444bb299d392988df75f
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998624

Reaction notes

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