Acetic Acid → 4-(4-Phenylnaphthalen-1-ylamino)phenol

HRID 503626Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Br.CC(O)=O>>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)=[CH:11][CH:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 67318488N-(4-Methoxyphenyl)-4-phenyl-1-naphthalenamine

Product 1

HCID 594273224-(4-Phenylnaphthalen-1-ylamino)phenol

Conditions

Temperature: 140 °C

Procedure

A round bottom flask was charged with N-(4-methoxyphenyl)-4-phenylnaphthalen-1-amine (600 mg, 1844 μmol) and 6 mL 1:1 HBr (100 μl, 1844 μmol) and HOAc (106 μl, 1844 μmol). The flask was fitted with a reflux condenser and the mixture was heated at 140° C. After 1 h, LCMS showed ˜50% conversion to desired product. Heating was continued for another 5 h. Upon cooling, the mixture was brought to neutral pH by addition of 6 N NaOH and extracted with DCM. The organic portion was dried, filtered and concentrated. The crude material was purified by silica gel chromatography, 0-50% EtOAc/hex to provide 4-(4-phenylnaphthalen-1-ylamino)phenol. MS: [M+H]=312.

Workup

customThe flask was fitted with a reflux condenser

Sources & evidence

ORD record: ord-80eecf4e406f4a0591a74583e4cb75eb
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776857B2

Reaction notes

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