Ammonia → 2,2'-Diamino-1,1'-dinaphthyl

HRID 844525Notes

Reaction equation

[NH3:1].S([O-])([O-])=O.[NH4+:6].[NH4+].[CH:8]1[CH:9]=[CH:10][C:11]2[C:17]([C:18]3[C:27](O)=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][CH:22]=[CH:23]4)=[C:16]([OH:29])[CH:15]=[CH:14][C:12]=2[CH:13]=1>>[CH:22]1[CH:23]=[C:24]2[CH:25]=[CH:26][C:27]([NH2:1])=[C:18]([C:17]3[C:11]4[C:12](=[CH:13][CH:8]=[CH:9][CH:10]=4)[CH:14]=[CH:15][C:16]=3[OH:29])[C:19]2=[CH:20][CH:21]=1.[CH:22]1[CH:23]=[C:24]2[CH:25]=[CH:26][C:27]([NH2:6])=[C:18]([C:17]3[C:11]4[C:12](=[CH:13][CH:8]=[CH:9][CH:10]=4)[CH:14]=[CH:15][C:16]=3[NH2:1])[C:19]2=[CH:20][CH:21]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 11762Binol

HCID 25041Ammonium Sulfite2×

Product 2

HCID 205712,2'-Diamino-1,1'-dinaphthyl

HCID 36177972'-Amino-1,1'-binaphthalen-2-ol

Conditions

Temperature: 200 °C

Procedure

Although it is reported that 2-naphthylamine can be obtained in high yield when 2-naphthol was heated to 150° C. in the presence of concentrated aqueous ammonia and ammonium sulfite for 8 hours, no reaction was observed when the same conditions were subjected to BINOL. When the temperature was increased to 200° C. and more ammonium sulfite was employed, NOBIN was exclusively formed without detectable amounts of BINAM. Thus, by extending the reaction time to 5 days and increasing the amount of ammonium sulfite to 10 equivalents, the starting material disappeared completely. The produced solid was simply filtered and washed with water. A 91% isolated yield of NOBIN was obtained by recrystallization from benzene. Thus, a practical procedure for the synthesis of NOBIN from BINOL in a single-step via a process that can be scaled-up in high yield is provided.

Sources & evidence

ORD record: ord-d804f7f133e1453287dc7f9865db7a6d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380392B1

Reaction notes

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