Acetic Anhydride → HCID 19027809, compound

HRID 2379620Notes

Reaction equation

HRID 2379620 reaction equation
NC1C([N+]([O-])=O)=CC=C2C=1C=CC=N2.NC1C(N)=CC=C2C=1C=CC=N2.[Sn](Cl)Cl.[NH2:30][C:31]1[C:40]([NH:41][C:42]([CH3:44])=[O:43])=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][CH:35]=[N:36]2.C(OC(=O)C)(=O)C.[CH2:52]([S:58][CH:59]([CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[C:60](O)=[O:61])[CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>N1C=CC=CC=1>[NH:41]([C:40]1[C:31]([NH:30][C:60](=[O:61])[CH:59]([S:58][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[CH:35][CH:34]=[CH:33]2)[C:42]([CH3:44])=[O:43]

Participants

8

Reactant 6

HCID 7918Acetic AnhydrideHCID 24479Stannous ChlorideHCID 1189016-Nitroquinolin-5-ylamineHCID 426874Quinoline-5,6-diamine2×HCID 14995420HCID 14995420, compoundHCID 19027847HCID 19027847, compound2×

Product 1

HCID 19027809HCID 19027809, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Commercially available 5-amino-6-nitroquinoline was reduced to 5,6-diaminoquinoline using a procedure analogous to that described in Example 34, except tin (II) chloride was used in place of iron. 5,6-Diaminoquinoline was converted to 5-amino-6-acetaminoquinoline by reaction with acetic anhydride and pyridine. Using the procedure outlined in Example 25, 5-amino-6-acetaminoquinoline and 2-(hexylthio)decanoic acid were coupled to give the title compound. Mass spectrum m/e: 471.3 (M+).

Sources & evidence

ORD record
ord-75e3015b989a4cc49ce1e2552a19adfb
Source dataset
uspto-grants-1994_11
Patent number
US05362878

Reaction notes

Loading…