Sodium Hydroxide → HCID 57471187, compound

HRID 1044486Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=3)[CH2:10][CH2:9][CH:8]2[NH2:19])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1Cl)CC1C2C(=CC=C(OC)C=2)CCC1N.[OH-].[Na+]>ClCCl>[NH2:19][CH:8]1[CH:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=2)[C:16]2[CH:15]=[C:14]([OH:17])[CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1

Participants

Conditions

Temperature: -10 °C

Procedure

1-(4-chlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (13.18 g, 43.7 mmol, prepared analogously to 1-(3,4-dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine cf. example 3) was dissolved in dichloromethane (200 mL). The solution was cooled to −10° C. and a 1 M solution of borontribromide in dichloromethane (131 mL, 131 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirring was continued for 2 h. The reaction mixture was poured on ice water and sodium hydroxide was added until pH 8 was reached. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was used for the next step without further purification. Yield: 8.89 g (30.9 mmol, 71%, colorless solid).

Workup

temperatureto warm to room temperature
additionwas added until pH 8
extractionThe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude product was used for the next step without further purification

Sources & evidence

ORD record: ord-ff9d31e168024c5ca772d1de6c279bf2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563617B2

Reaction notes

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