4-Bromoaniline → Acridine, 2,9-diamino-

HRID 2275516Notes

Reaction equation

HRID 2275516 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[C:13](CCC(O)=O)[CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.BrC1C=CC([NH2:26])=CC=1.O=P(Cl)(Cl)Cl>>[NH2:26][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[C:2]([NH2:1])[C:3]3[C:8]([N:9]=2)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:14]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 24813Phosphorus oxychlorideHCID 57859223HCID 57859223, compound

Product 1

HCID 31624Acridine, 2,9-diamino-

Procedure

Ullmann reaction (Step 1) of 2-chlorobenzoic acid 1 and 4-bromoaniline 2 afforded 4′-bromodiphenylamine-2-carboxylic acid 3. Cyclisation with POCl3 followed by amination gave the expected 3-bromo-9-aminoacridine 5 in good yield and purity.

Sources & evidence

ORD record
ord-5e7fb896412b42a0a38279209d9cacd2
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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