4-Methoxybenzoic Acid → HCID 20371624, compound

HRID 616216Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[Cl:12]C(OCC)=O.Cl.[NH2:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[OH:34])[CH:23]([OH:30])[CH2:24][NH:25][C:26]([CH3:29])([CH3:28])[CH3:27]>CC(C)=O.O>[ClH:12].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:19][C:20]2[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=2[OH:34])[CH:23]([OH:30])[CH2:24][NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:9])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 4-methoxybenzoic acid (0.76 g, 0.0050 mole) and of triethyl amino (0.70 ml, 0.0050 mole) in dry acetone (8 ml) was cooled to -15° C and ethyl chloroformate (0.54 g, 0.0050 mole) was added dropwise. The mixture was stirred 30 minutes at -15° C, and 30 minutes at 0° C, and then cooled to -15° C. A solution of 3-amino-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride in acetone (10 ml) and water (1.7 ml) was cooled to -15° C and added to the reaction mixture in one portion. The solution obtained was stirred at -15° C for 30 minutes, at 0° C for 30 minutes, and at room temperature for 1 hour. The solution was evaporated in vacuum and the residue was recrystallized from water yielding 1.02 g (52%), m.p. 224°-225° C of the title compound, identical to the compound prepared in Example 5.

Workup

temperature30 minutes at 0° C, and then cooled to -15° C
additionadded to the reaction mixture in one portion
customThe solution obtained
stirringwas stirred at -15° C for 30 minutes, at 0° C for 30 minutes
waitat room temperature for 1 hour
customThe solution was evaporated in vacuum
customthe residue was recrystallized from water yielding 1.02 g (52%), m.p. 224°-225° C of the title compound, identical to the compound prepared in Example 5

Sources & evidence

ORD record: ord-582f8e8776ba44b0a29882f4e9624a95
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04072760

Reaction notes

Loading…