Ammonium Acetate → 5,6-Dichloro-indan-1-ylamine

HRID 839519Notes

Reaction equation

HRID 839519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=O)[CH2:6][CH2:5]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:19].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[CH:7]([NH2:19])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 229036095,6-Dichloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 203234005,6-Dichloro-indan-1-ylamine

Procedure

Following the procedure of Example 1, 5,6-dichloro-1-indanone was reacted with ammonium acetate and sodium cyanoborohydride to yield 5,6-dichloro-1-aminoindane; yield = 670 mg. The crystalline compound was treated with 360 mg. of maleic acid in 25 ml. of isopropanol. The maleate salt crystallized and was separated by filtration. Recrystallization of the salt from a 1:3 isopropanol/ethyl acetate solvent mixture yielded 650 mg. of 5,6-dichloro-1-aminoindane maleate melting at 167°-170° C.

Sources & evidence

ORD record
ord-ff672ca82f8f47aca19d173fbfa32228
Source dataset
uspto-grants-1978_06
Patent number
US04096173

Reaction notes

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